I also am retired, though my interest rekindled a number of years before retirement. So I asked myself the same questions. Here is my suggestion. Consider just getting an old computer with Windows 95 on it, or install a copy. I did this 8 or 9 years ago. Sounds old fashioned, but the elegance of this is that I load classic DOS and early Windows games on this computer and simply go turn it on when I want to play them. Yes, I know about XBox. But all the times I’ve upgraded computers or operating systems, I never had to reinstall or tweak anything. Most classic games install through their setup program, and require no special effort, though some might install from DOS. My old computer just sits there waiting faithfully for me. That is the point, isn’t it, and truthfully, it’s the lazy man’s way. Now if your thing is the challenge of making your new stuff do old things, go with XBox. That’s just not my interest. I cut my teeth on DOS and Windows 3.x, and beta tested Windows 95, so I find it fun to occasionally revisit. Anyway, 95 is about the last Windows with enough DOS to run all the old classics like the DOS version of KQ1 and a number of the xp games are backwards compatible, so you’ve got a pretty good range of classics. Without tweaking, ’95 has a clock limit so what you need is a Pentium 1 or 486. The “C” version will even support USB with proper device drivers. These old computers show up in thrift stores fairly frequently at about the $5 – $10 price range, and a nice clean looking one will likely be already set up and even have floppy readers if you’re lucky enough to have the old disks. I have 3, one in operation and 2 in reserve (two were free so gee, a $5 investment) so I’m set. One is even running DOS/3.1. The sad thing is that I made a move about 13 years ago and tossed all my classic Sierra games –all on 3 1/2 floppies. I realized my mistake and use to see the old games frequently. Would buy just to restore what I tossed, but now the old Sierra stuff just doesn’t show up much anymore. Good luck and enjoy.