I loved all of the Sim games and Roller Coaster Tycoon games. I was addicted to SimCity 2000 back in the day, and I'll still occasionally play it.
I have SimCity 2000 (with Urban Renewal Kit), SimTower, SimIsle, SimCopter, Streets of SimCity, SimFarm, SimCity 3000, Rollercoaster Tycoon (with Corkscrew Follies and Loopy Landscapes), and Rollercoaster Tycoon 2.
If I know anything about the old Maxis games, Aaron, they use 16-bit installers, so they won't be able to run on Windows x64. You might be able to try to install the game on a 32-bit system, like you've already done, and copy the program files over to the 64-bit system. If that doesn't work, you can play the games in a Virtual Machine, like I do.