I'll reply to each point (including the other replies).

But before I do:
The question here is not, "are PCs better than Macs?" or "are Macs better than PCs". That's a stupid religious war to get into. The question is "how to convince a PC user to switch?"

1) Given that the two platforms are ~ equivalent w/r to features and capabilities, there is no compelling reason to switch one way or the other between the two platforms given features.

2) My contentions is that moving users PC->Mac is stymied by the large factual price delta to "go Mac" between the platforms. Given #1 above, overcoming the price delta between the two platforms requires something fairly compelling.

3) There is no quantifiable compelling reason to switch PC->Mac and several quantifiable compelling reasons not to, price being one of the major ones.

In response to your points.

The typical user upgrade path between Microsoft OSs has been 95->98->XP->Vista (and now I suppose XP->7 and Vista->7 depending). Me was DOA and 2000 was not generally used by consumers, rather it existed principally as a server OS.
"Apple has just come out with OS updates faster than Microsoft. Back in the day, you could have bought Windows 95, 98, Me, 2000, and XP in the same time that it took Microsoft to come out with Vista after XP. (You can even go back further if you ignore Vista like most did). And if you bought each of those at retail, it cost a lot more than $129 each time (even for upgrades)."

In actuality MS has released a similar number of updates from Windows 95 -> Windows 7 as Apple has from System 7.5.1 to OSX 10.6.1. Ignoring the differences in versioning schemes used by the two companies. The actual OS path for Windows users has been
95->95SP1->98->98SE->XP->XPSP1->XPSP2->XPSP2b->XPSP2c->XPSP3->Vista->Vista SP1->Vista SP2->Vista Platform update
Which, going by what Apple calls "major releases" is 14 major releases.

The only purchase cost was on major name changes (so 95->98->XP->Vista). These were typically upgrade costs or shipped with new systems and bundled in at OEM pricing. So for example, I got XP for ~$50 (OEM) and now 8 years later still have a modern, updated OS to play on at $0 additional dollars.

In a similar time period Apple has released
7.5, 7.6 (which was DOA), OS 8, OS 9 and OS X (10). It's confusing because there is quite a bit of overlap between some of the versions (X came out when 8.5 was still being serviced)...
I'm going to go out on a limb here and say that the typical upgrade path was
7.5->7.6->8->X...which is fairly similar to the Windows world. Even figuring the need to purchase new hardware in the transition from 680x0 to PowerPC to Intel, it really wasn't that different than buying new Windows Boxes for new Windows. So that's a pass.

But let's look at contemporary OS's. XP v X. They came out ~ the same time. But I'm still using a fully updated XP OS at $0. Can you say that X10.6 had a $0 migration path from X10.0?

> Macs can use the same mice/monitors as PCs (assuming you don't have an all-in-one like an iMac), so that argument is moot. Funny thing. I'm using this great new mouse with my Mac. I like it a lot, but it did cost $50. It's a Microsoft wireless mobile 5000. Works great.

Good, another reason not to switch. And proves my price point, err...point. You can get reasonably good hardware for MS boxes, that work on Apple boxes, at better prices. This is what you ultimately ended up doing.

> You can use any number of text editors on a Mac or PC. Some are free, some cost money. It's silly to pick a random Mac-only editor that costs money and compare it to "thousands" of PC ones that are free.

It's by way of an example. Other examples of overpriced basic featured software abound in the Mac World. They are usually released with quite a bit of fanfare and Jonny Ive style breathless showcase videos filmed with too much zoom talking about how this piece of underpowered software will change your life if you spend $25-$50 on it.

Not a reason to switch.

> In Microsoft land, I don't think that the Leopard -> Snow Leopard transition would ever have happened. Microsoft would never have made that upgrade. They might have pushed it to a service pack, but I doubt it. Microsoft probably would have held it back to wait for the next major update. There were major differences in the underlying system, but not much that was user visible. This is why it cost $29. It's not because it was only worth $29... it's because it's worth it to Apple to push people to upgrade. So, instead of getting the updates out as fast as possible, I think Microsoft would have waited. Also, $29 is more than worth it for those of us who wanted Exchange support built in.

Which is exactly the point. In Microsoft land 10.5->10.6 would have just been a SP release.

Again, paying $29 for something I can get for free on the other platform is not a reason to switch.

Digging deeper, your argument is that I can spend 2x for a box to run an OS I have to pay to do minor version updates on, so I can just use all the same bargain hardware I'm using on my PC (and oh yeah, you'll have to repurchase all your software again, or buy a VM and Windows again at even more cost)?

Not the strongest line of why someone should switch I've heard yet.

This carries over even into Apple's advertising, which basically amounts to either "buy a Mac to be cool" or "buy a Mac so you can appear to be smart". Great. Not sold.