Stop using apple products. They are luke-warm in design and terrible in execution.
Get a PC: Supports Linux, windows, all your games (ALL) and has a mouse with more than one button.
> all your games (ALL)
This is measurably untrue; modern computers have trouble with the Windows XP era of games a lot of the time. Many games require tinkering and some will just crash after a minute.
This is mostly the fault of games and not Windows. Software usually breaks because of unfounded assumptions, for example, that user documents are always at a specific location or that CPU frequency is always constant. Instead of using Windows API functions to retrieve the path or keep track of frequency, lazy developers often halfass the implementation, hardcode values into their code and that breaks sometime in the future when those API functions become meaningful.
Yes, there will be some amount of inevitable jank, but by and large the latest version of Windows will happily run software originally written almost 30 years ago for Windows 95.
Macs have had a second mouse button for 20ish years.
Unfortunately 16 bit Windows applications no longer work. I don't believe that is being actively worked on.
DosBox works well enough for most pre-Windows stuff, DosBox-X can handle the Windows 95 era well enough, but Windows 2000-Windows 7 stuff is actually kind of hard to get fully working on modern computers, and I feel emulation has not been able to keep up.
I wish a lot of success on this project. It would be great to get Jazz Jackrabbit 2 working on my Mac without mucking with VMWare.