I played most everything that was available up to 2005. I stopped after a few expansion packs for The Sims 2.
Sim Copter and Streets of Sim City are now playable on Windows 10, with "Patches" from Alekasm:
http://simcopter.net/
http://www.streetsofsimcity.com/
Sim Copter and Streets of Sim City are unique to the Sim franchise in that you can use Sim City 2000 maps in each game. Sim Copter is simply about doing missions around a city (Extinguishing fires, catching criminals, MedEvac missions, transport, rescue missions, etc.) Streets is a crappy (but mostly enjoyable, IMHO) B movie grade game where you go on one of several 1970s TV show career paths. Both games feel cheap in a way, and you're definitely not gonna get realistic physics for the cars is Streets, but I can't help but enjoy them. Streets is still playable online, if you use Hamachi and the LAN option.
EDIT: Apparently, Streets isn't yet playable online.
Both Sim Copter and Streets are still playable on Windows 10, though. You do need to use some "Patch" programs that Alek made, though. Here's the patch site for Sim Copter.
http://www.simcopter.net/
- Austin