When I get the time and motivation to touch Hammer again I have to remake gm_municipalairport... because your first map always sucks
The original System Shock is an MS-DOS game which was ported to Windows 9x later, so I'd count it as a DOS game. Either way, never played it - but when I think of early Windows games I think of SkiFree, JezzBall, Glider and SimCity 2000 among others.
Speaking of old Windows computers, I picked up a Compaq Contura 3/25 that is now undergoing my repairs - the CCFL tube went bad and subsequently fried the LCD inverter board, which is always nice...
Not a big console guy myself, but I do have a Wii U and two GBA systems along with games.