It is definitely subjective, however it's easier to talk about when everyone discussing it has experiences with both sides. I've lived with Windows, Mac OS X, and Linux daily for years now. Were as you said it right at the start "Just months after planning a break for the world of Mac, I'm planning on diving further into Windows." If thats what keeps you happy, thats good. It just pains me a little to see that you came really close to making the leap of at least trying a Mac as a personal machine, then backed off and now have issues. Sure, the upgrade situation isn't that big of an issue, but to me, it's one more minor thing that is added to the mountain of issues I see on the Microsoft side. I don't directly want Microsoft to fail, but their bad decisions affect me daily. Be it their horrible security that led to hours of my time wasted when people used Microsoft products to browse these boards, or the bad decisions that lead to frustrations dealing with Microsoft servers at work.

The reason your decision pains me a bit is that it mirrors my situation about 8 years ago. I was a big Microsoft only person, shrugging off Linux and Mac OS. I was happy, even when Windows 98 would blue screen on me. After all, 2000 was right around the corner, and it was so much better. What changed my situation though was wanting to be legitimate, as well as running a home server. Windows Server licenses are pricy. Software to add more functions to Windows is pricy. So I decided to get my feet wet with Linux, and eventually learned enough to have a home server that ran as a router and file server. It grew over time into much more. I then got a job supporting servers, and my Linux knowledge allowed me to grow into other Unix systems as well. When OS X was released, I looked into it due to the Unix underpinnings, and was pretty much sold on the spot. It took some time, but I saved up to buy a refurb iMac to try it out. Over time, I found myself using the iMac more then my custom built PC, and ended up buying another more powerful Mac. And from there, I just started replacing machines with Macs as I needed.

Some of my posts are also of the venting nature. For that, I apologize for the parts that came across rude. Tech is a major part of many of our lives, mine included. And at times, I can get very passionate about it. In the end, if your really happy with your situation, thats good. I still urge you to try out the Mac side at home some day, and I'll even offer what advice and support I can if you do.