It's worth noting that not all 575s have CD-ROM drives... but aside from that, I personally think finding a way to install 7.5.3 from floppies should be mandatory for all new recruits – it builds character ;-)
Do either of them have ethernet? If not, I'd make that priority number one... it will make your life a lot easier and the NICs for those are (generally) cheap and plentiful. The 575 is a better machine than the 580... I have a couple that still get used daily. If you feel like throwing a few bucks at it, you can get a quick and easy performance boost with a 32MB RAM module and a 7200RPM hard disk. Both are pretty affordable upgrades if you shop around.
I'd actually prefer to install by floppy so I can put all of these floppies to good use

But a CD works fine as well since both computers have CD drives
I've yet to have the chance to install ethernet ports. As soon as I scratch up some more money it's the first thing going into them. All of the other upgrades are going to have to wait until I can figure out the other problems and whatnot :-/
OP, it is up to you what one you want to play with first, but, since you will eventually use em both I would not say that it such just a big deal and you can choose what you like more based on your experiences with them.
So far, I like them both. But each of them gives me their own issues. The 580 doesn't read CDs right anymore, the 575 is still giving me blank bomb messages when I try to explore the hard drive, and the clocks on both don't work.
That is a classic problem. What other programs do the hard drive have? Many Internet-related programs has a built-in MacBinary decoder.
From what I have seen, nothing internet-related. They don't have ethernet ports just yet, and as far as I'm aware these things were used for educational games only in that school.