@MontrealCL
Hi and welcome :-D
How ironic, I actually find myself wanting to get an Atari after years of being an amiga user. I guess its that all over nostalgia thing. And those CT060 cards for the falcon look damn tasty too (not to mention the Hades (IIRC) set up) :-D
The A500 may be old, but assuming you get hold of Kickstart3.1 and a CD Rom (for installation purposes) theres no reason you cant run the most up to date 680x0 version of the OS (v3.9).
Comparisons are a little trickier. The 40MHz 68030 is faster than any "standard" 030 based machine released by commodore back in the day, so it is faster at code crunching than the A4000/030 and A3000 which used an 030 at 25MHz. Of course the A500 still has the original chipset which puts it graphically behind the ECS based A3000 and AGA based 1200/4000.
As for installing software on the HD, if its old "custom disk format games" that wont install, check out
www.whdload.de where you will find a massive collection of HD installer / patches for old games and software.