It seems that every time Apple is close to a new release of Mac OS X, I’m here begging and pleading for a decent upgrade path for recent purchasers of new Macs or the previous Mac OS upgrade box. Of course, Apple doesn’t pay attention and they do what they planned to do anyway.

However, I think my argument becomes ever stronger with each upgrade, for various logical reasons, at least that’s what I believe.

When Mac OS 10.0 became 10.1, of course, the upgrade was essentially free, unless you ordered for shipment direct to your home, in which case a $19.95 “shipping and handling” fee was required. Lest we forget, that fee was the subject of lots of heated arguments about Apple’s alleged profiteering ways.

Regardless, 10.1 was sort of usable, but still slow as the devil, even on the fastest Mac of that era. Come 10.2 and 10.3, and things got a whole lot better. Now, though, you had to pay the full $129 for the upgrade, unless you bought a new Mac after the shipping date was announced — usually at the latest possible moment — in which case you’d be eligible for a special upgrade plan for a brief period of time. How long? A few months or maybe longer, depending on when the next version of Mac OS X was due.

In each case, however, the upgrades were well worth the money because an almost usable operating system became better and — unlike a certain company headquartered in Redmond, WA — faster and more stable. Come 10.4, Mac OS X finally realized its industrial-strength potential, and it became a mainstay for millions of Mac users, both new and converted.

Now it’s fair to say that, despite the promise of over 300 nifty new features in Leopard, it’s not going to be an easy sell. For one thing, just what Macs will Apple leave behind? Officially, the final system requirements have not been announced, and I won’t take any of the comments in rumor sites as gospel. Besides, things are apt to be in flux until Apple begins to take orders.

But it’s fair to say that Leopard’s new graphic eye-candy, such as Core Animation, is apt to require a decently-fast G4 with a powerful graphics card, which probably means that most anything Apple produced in the last four years or so should be compatible.

In the scheme of things, that doesn’t seem too bad, considering that the full Aero 3D interface for Windows Vista barely runs on many of today’s PCs, and far fewer models that are more than a year old.

Apple, however, has said nothing about whether Leopard will be faster, although I would assume they’ll try to make it more stable, particularly the Finder. While the Finder’s new look and features may seem sexier to tout in ads, if it is subject to fewer multithreading slowdowns, that would be just as important, if not more so.

However, does all that, plus Time Machine, Spaces and the other new features, total up to sufficient justification to buy yet another operating system upgrade from Apple at full price? My decision is clear. I will order a family pack the day it goes on sale, and install it on all my Macs as soon as it arrives, although separated by a few hours, to make sure that the setup process works reliably.

But I’m an early adopter, despite the well-known risks. If you depend on your Mac to help you earn a living, you can’t be so cavalier about installing a brand new operating system version, even if Apple makes the installation process nearly foolproof.

What, for example, about the applications you need? Will they be compatible, or crash with abandon or function in a crippled fashion. You probably won’t know until the dust settles, and that may take at least a few days before the Mac troubleshooting sites report the news you need to know.

In the meantime, if I were in the driver’s seat at Apple, I would want to do whatever I could to encourage you to buy that upgrade. If this meant having, say, a longer grace period for recent purchasers of new Macs and Tiger upgrade kits, so be it.

Personally, whether Leopard comes out at the beginning of October, the end of the month, or somewhere in between, I think Apple should begin to accept orders for upgrades right after Labor Day. Yes, I know they apparently plan to unveil new iPods that week, but that’s beside the point.

What’s more, on that day, anyone who buys a new Mac or Tiger box ought to be eligible a free Leopard upgrade for, say, $9.95 a copy. No questions asked, and no installation restrictions, which means they send the same DVD that the full retail purchasers receive.

Of course, as usual, Apple never listens.

Months before the iPhone debuted, Apple was being asked over and over again about the prospects for running third party software on it. But a short time before the hot-selling gadget shipped, Steve Jobs was saying that Apple hadn’t decided how to handle development for the iPhone yet, but that a workable solution might come at a later time.

Not long thereafter, during his WWDC keynote, Jobs said that developers could build Web-based applications using Safari, but there would be no other supported method. Was that meant to close the door permanently, or just to give Apple more time to develop a secure solution?

Now it’s not as if the iPhone is bereft of software. Apple provides plenty of useful tools, including as full-featured a browser as you can expect on such a device. But what about the stuff that hasn’t arrived yet, such as a chatting application and other niceties?

True, some of this stuff is arriving clumsily via the Web-based interface, but it doesn’t integrate so nicely with the iPhone’s features, such as the icon dock. So call it half a loaf, and it’s a sure thing developers are anxious to get something more flexible and far-reaching.

Right now, though, it appears they may not require Apple’s help.

As you recall, during the first few months that Apple built Intel-based Macs, running Windows wasn’t so easy. Microsoft’s VirtualPC wasn’t compatible, and other solutions, from small companies, were barely functional. However, some crackers found a way to patch the firmware to allow installing Windows on another hard drive partition. After some folks won a prize for their work, Apple came out with an official solution. In fact, it arrived so quickly, you just knew it was lying in wait for the appropriate occasion to release.

So how does the Boot Camp example relate to the iPhone? Well, right now, a lot of smart programmers have played with the iPhone’s OS X-based underpinnings and have found ways to take it way beyond the initial Apple design. Just this past weekend, you probably heard that a teenager had devised a way to unlock the iPhone, so you could plug in a SIM card from another network, say T-Mobile in the U.S., or an overseas carrier, and it would be mostly functional. Mostly functional meaning that such features as visual voicemail and YouTube support are lacking. Those features evidently require a connection to the AT&T network, and no doubt other networks that will come to support the iPhone will have to make similar adjustments.

Unfortunately, the method mentioned most often requires opening the phone and fiddling with a soldering tool to accomplish some of its magic. But there are others who tout software-only tools that have the same end result.

But even if you don’t care about cutting the ties that bind the iPhone to AT&T, there are other options that allow you to install third party software. Some allow you to use Mac OS X’s Terminal to send Unix software on over to the iPhone, and others allow you to install more user-friendly chat clients and other stuff.

Speaking of user-friendly, there’s also a site now that offers an installer application that greatly simplifies the process of adding new stuff to your iPhone.

Some of this is reminiscent of the early days of Mac OS X, when the operating system didn’t have a whole lot of features, and even printing was uncertain. But there were plenty of third party applications that unlocked the Unix core to put friendly faces upon different tools. Some were just interface-related, such as allowing you to move the Dock away from its bottom center location. Apple eventually took the hint and allowed you to move it to the left or right side, but placing it on the top or in the corners is still reserved for those system interface tuners — or, if you prefer, a set of commands in the Terminal.

In the same fashion, you can bet Apple is watching the iPhone hacking world very carefully, since they fully expected the scene to play out this way. First, of course, they want to make sure that the hackers aren’t doing something illegal, sufficient to call the legal eagles into action. But even if this stuff is perfectly legal, if lots and lots of iPhone users flock to these newfound toys, I’m really sure that Apple will take the hint and do something about it.

Of course, you’ll no doubt see a fair number of additional applications and system-tuning tools in future iPhone updates. These will be the officially-sanctioned solutions. What’s more, I wouldn’t be surprised if Apple eventually opened the platform and provided a true Software Development Kit (SDK) to members of its developers program.

But providing an SDK doesn’t mean a simple set of applications to create iPhone software. Apple has to test those tools, and provide developer support in some fashion. Those who pay the big bucks for these developer programs are entitled to varying degrees of support, depending on the package they purchase. That means Apple has to allocate engineers to the project, and right now they no doubt have their work cut out for them, finalizing Leopard for the planned October release.

I fully expect that Leopard will, hook or crook, appear before the end of October. What’s more, I fully expect that once Mac OS 10.5 is out the door, Apple will put the final spit and polish on a fully-featured iPhone programmers tool. The hackers may have shown the way, but Apple will eventually deliver the goods.

I can sense the responses now from some of you. That crazy Night Owl is going after Microsoft once again, with another unprincipled or at least severe attack. However, this particular commentary doesn’t have a whole lot to do with the quality of Microsoft’s software. Instead, I’m more concerned with the blatant example of corporate paranoia — or greed — that just serves to make people more upset with the company.

Now as everyone who has used Windows in recent years knows full well, Microsoft has an online activation feature, a process of registering the software with the company via your Internet connection. If you you fail to activate, the software is mostly or completely crippled within 30 days.

However, online activation isn’t exclusive to the world’s largest software company. In fact, Adobe is just as guilty as enforcing a similar process upon its users. So in order to use the Creative Suite, after enduring a lengthy installation, you have to go through this one-time activation process.

Well, one time unless you happen to move your stuff to another computer, where you have to go through it all over again, although the process is simplified if you deactivate the software, first, on the computer you’re leaving behind. But most of you wouldn’t remember that critical step — I know I usually don’t.

Story continued in this week’s Tech Night Owl Newsletter.

As much as the Mac has been marketed as “the computer for the rest of us,” their definition of “us,” as often or not, was regarded as the well-heeled through much of the company’s history. Indeed, the progenitor of the first Mac, the Apple Lisa, cost roughly ten grand, way beyond the budgets of most people who might have been the product’s target audience.

Even at $2,500, the first Mac was considered a costly machine, considering that it came with very little software, and limited expandability. They say first impressions count for everything, and it’s quite possible Apple’s reputation for selling overpriced, underpowered hardware began then and there.

To be sure, after Steve Jobs was bounced from the company, executive greed resulted in keeping Macs expensive, so businesses seeking commodity hardware were easily shut out. Microsoft was only too happy to convinced them buy a cheap PC clone and struggle along with the various and sundry attempts to make the Windows “shell” function on its MS-DOS foundation.

I don’t want to say that Macs were necessarily bad way back when. I owned a number of them during the early days, and no other personal computer was as user-friendly, reliable and productive. And that’s before the mass market’s acceptance of the Internet, and the malware plague that engulfed the Windows platform.

Yes, some home users and most content creators came to adore their Macs, but you could hardly call that a mainstream audience. Apple’s bad rap over the years remained the same, that Macs were expensive playthings for the wealthy and there wasn’t enough software available. Business users? No company in its right mind would ever consider a Mac except for the eccentrics in its graphics department. They aren’t meant for “serious” work, such as spreadsheets and word processing.

One of the most important changes that Steve Jobs made when he took over as Apple CEO a decade ago was to get rid of the dead wood. As many executives were apt to do when fixing a troubled company, Jobs moved Apple back to its core business. Forget digital cameras, printers and even the Newton. Build the best personal computers on the planet and make them affordable for regular people.

So, in 1998, you could consider the first Bondi blue iMac, listing for $1,299, as quite affordable for an all-in-one computer, although it would take years for Apple to lose most of its reputation as building premium-priced hardware. Even today, some still believe the Mac is necessarily more expensive than a comparably equipped PC, but that’s no longer true.

For a time, though, it seemed as if the best Jobs could do, with all his pomp and circumstance, was to deliver flashy products and essentially keep Apple from shedding any more market share, although it did continue to drop for a while.

However, there has been a confluence of events that has made it possible for the Mac to, at long last, become a genuine mainstream product. I can’t say whether this was what Jobs and his cohorts at Apple planned this all along. Sometimes things just happen, and a smart executive will know how to take advantage of a good opportunity when it arises.

In this case, the opportunity came in a roundabout way, first with the iPod. Did Apple know they’d sell 100 million of those things in the space of a few years and come to own the digital music player market? Was that something they planned all along? Well, maybe they had hopes that it would ultimately expand to the Windows platform, and that iTunes would overtake the market and become a top-tier music retailer. But nobody is that smart. They were in the right place at the right time.

The iPod also gave PC users a direct exposure to Apple technology, and they were able to compare those gadgets to the growing misery of keeping Windows running properly. Microsoft also did its share to shoot itself in the foot, taking years to build Windows Vista, which has garnered a well-earned reputation as being slow, resource intensive, and unusually buggy. Many businesses just won’t touch it until the SP1 update, in the hope the most serious defects will be addressed. And, in fact, many customers order their new PCs with Windows XP, and will absolutely not accept Vista, at least for now.

In contrast, Macs seem to just purr along. Yes they’re far from perfect, but most of the ills that engulf the PC platform rarely occur on Macs. Spurred by extraordinary demand for Apple’s note-books, and growing demand for its desktops, the company has reportedly moved just behind Dell and HP in U.S. retail sales recently, and few are suggesting that Mac sales have reached a plateau.

Current expectations call for sales of over two million Macs in the current quarter alone, and calling them mainstream is no longer a pipe-dream. It’s a reality.