The main game I'm trying to get to work is a Windows 95/98 game called Star Wars Episode I Racer.

There is no such thing as a durable joystick, I don't think. The real device I like to use is a Microsoft Sidewinder Force Feedback Wheel and Pedals, which I have, but for compatibility purposes, I'm trying to get the game working with the Logitech Joystick, which I picked up for $2, first, just to get things working before attempting the Sidewinder.

I was thinking my odds will be better with the newest Wine I can get. I did find someone with the game working with 1.7.x wine, but other than that Arch Linux was used, I don't know the details of the configuration.

I have installed Ubuntu before and it was not to my liking, being pretty locked down compared to debian, IMO

I don't think a SATA adapter will fix anything