You're probably right about the "thousands of dollars", when 2K came out, we were still willing to work with MS products, and bought a couple of copies at that time. Thousands of dollars pretty much sums it up.
I agree that they keep getting better, but I would feel much more comfortable if they hadn't used the unsuspecting public as guinea pigs for the last 15 years or so. We keep two XP boxes; the first because I couldn't pry my partner's laptop out of his cold dead hands and the second because we opted to use a commercially available microprocessor simulator designed for Windoze instead of taking the time to re-invent the wheel. If we get some free time, I'm going to write the simulator to run on the AS/400...then XPbox[2] can be Sh!t-canned...
That said, we have "relatively" little trouble with either of the machines, though his laptop is more stable--of course, it's core duo, with GBytes of RAM, too. Which is the other thing that just floors me--Windoze is such a resource hog. Year after year, instead of making their OS better, they make it bulkier.
So, I don't really trust Microsoft, which is sad, because one of my partner's oldest friends works for them. I can recognize that each subsequent version of the OS is more stable and reliable than the last, but I also feel they should have had Win95 at that level before they released it--which means they've had a "less than acceptable" reliability level for the last 12 years or so...Not a great way to instill confidence.
