If you like to tinker, MS is the way to go. Tons of options, forms and price points.
If you need to use a computer to get stuff done, stick with Apple. Fewer, better, more integrated options.
It’s not a character flaw to have a preference. You are a good person either way and you can change your mind, or even use both! No demerits apply.
I find, over 40+ years as an engineering professional, that the Apple solutions are less expensive in nearly all interpretations, regardless of their initial price. It’s not unusual for me to work weeks to solve an MS problem, mostly due to the Microsoft/Non-Microsoft vendor conflicts inherent in their system…. Surface is the first consumer effort that tries to solve that, and it looks great. I’d buy one, but at my stage of life/career I have enough hardware. And 100% of what I own works perfectly (iMac, iPad, iPhone, Apple TV, Apple wirely routers and backups, and a nice, dusty, spare Dell with Win7, not connected to the internet.)
Works for me. Don’t make too big a deal of your problem. Your post was entertaining, but solving your problem is really easy with a checkbook. If you can do that, it’s not really a problem.