The 500 is the same motherboard as a 2000 minus the Zorro 2 slots and video slot(the side car slot on it however is the same as Zorro 2 digitally). With a 530 accelerator it's closer to a stock 3000 in power though. There are a slew of programs for serial based transers, using a normal 5pin crossover connection. Pc2Am for example.
www.aminet.net, and it's mirrors are the best place so far for free software on amigas. The usual 500 has KS 1.2 or 1.3 chips on it, you can run the 1.X workbenches on it. You need a better kickstart for later versions of the OS (at the cost of losing a few games). If workbench can't detect the files on a diskette that is self booting, it's doing some copy protection, not sure how to break that. Using the Workbench disks you can format the harddrive and install the OS. No clue on terminal programs.