I'm not a machinist, I'm a lot like the OP, except that I have known and spent some time in machine shops and even worked in a few when I was younger. I agree, community college classes will likely be the best (and you'll likely be able to make some things you'd like on their machines and have the instructor there to assist you). I'm also likely a good ways off from being able to do this, getting the machines I mean.
We'll be turning the carport into a shop (soon) and I'll be able to rewire and pipe it how I please. I plan on putting a vertical mill in eventually with (hopefully --I'll probably have to give in for smaller) a 24x48" table, and a bed lathe in it, I'd like 4'. Manual machines converted or updated to at least have analog/digital displays (NC?). I'll likely take a year or so before I actually get one after I get the shop done.
What I'll mostly be looking for is a situation where grandpa died and the family has no idea what to do with the stuff in the garage. That's where you'll get the best deals and all the tools and, hopefully, whatever upgrades he may have put into it. Maybe even some raw materials thrown in.
Auctions may be worth looking at, but you may have to frequent a few until you find one where nobody shows up hellbent on getting a new machine for their business and willing to pay for it.
Another would be a machinist retiring and selling his home setup, but that may cost you since he'll still be alive and he'll know exactly what it's all worth and will be likely trying to get all he can.
Whatever you do, stay away from the 3 in 1's or 2 in 1's. The mini lathe/mill setups. I've heard from a few good folks I trust that those aren't made well enough to do precise work and last. Even the Grizzly models, even made in USA stuff.
I'm aiming for Bridgeport gear if I can find it, and I know I'll have to save for it. And I have to look for absolute rock bottom prices, but patience and persistence is what pays off here. I may go look for one at DRMS when I'm ready. They may have one to give away. You hear "you pay for what you get"? Well, it goes for this too, just that you can find really good deals on good machines IF you look for a long time.
Luckily there are LOTS of machinists here. Good luck.