i've took the jump and play some of these old games myself. Dosbox so far hasn't failed me as i am also using it for blake stone and Duke nukem. but thats from my personal experience.
You supply no system specs,
IMO,hold off for now,it's a bit buggy for some.
I tried it for a week,not impressed,gone back to 8.1.
Not to mention the forced auto update/advertising/missing free features/questionable privacy settings.
p.s.running Pro version.
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My experience with W10 so far has been very positive. I would echo some of goodplay's points above (particularly privacy settings), but that can be easily fixed with a bit of tinkering, if you're into that (which I am).
I don't know if I could vouch for DOS-era games, but I've been able to run games as old as y2k-timeframe with no more issues than when I used 8.1. Ex: Rogue Squadron, Jedi Knight II, KoTOR. (is someone here a Star Wars fan...?) I also briefly tried the original Dark Forces, which uses DOS Box, and Sim City 2000, very briefly, but they did run.
**Knock on wood** I haven't run into any compatibility or stability problems with W10 yet, so I'd def recommend taking advantage of the upgrade while its free. Of course, that still leaves you a lot of time. Hope this helps!
I think most of the privacy stuff is because of tying to a microsoft account. try telling it that you don't have email and go that route. As far as auto updates, there is a setting that essentially stops it from the auto restart giving you a chance to hide the updates although i think you have to use another ms program for that. not sure though.