The one who probably provided me the most trouble and headache over the years is my favourite anno, 1404 history edition

I just use a single Bottle's bottle to install a bunch of off-Steam games. Contains many older windows dependencies; you have to install them yourself but they are found within the bottle's settings.

I remember trying to get Sims 3 working for my partner, it had all sorts of missing textures, kept crashing and had poor performance. Turns out you need a 4gb patch?? made from the community? Decided to toss it in my bottle and it works flawlessly. Have not tried dos games but may be worth a shot.

From steam, to lutris to base wine to he to trying a couple back cause nothing else worked.
Saw it all, did it all and I hazard a guess I soon will see it all again