Jarrod H - you posted "I want this thing to be affordable, easy to maintain, and something I can adapt for different uses and implements, and semi classic."
You're getting alot of responses that may be a little hard to decifer. In my view all IH Cub Cadets will fit your "want". With regard to the affordable part, this is relative to how well it is and has been maintained, and what you consider reasonable value.
Now, getting down to the nuts and bolts - what most are trying to tell you is that you'll eventually "want" a tractor for each of your implements. One for mowing, one for pushing snow, one for throwing snow, one for tilling your garden, etc. One tractor can do all these things, but the attachments have to be correct models for that tractor. There isn't one tractor that accepts all attachments or that adapts to all attachments.
I see Jeff B recommended a Model 149, which is a wide frame "hydrostatic drive" tractor that came standard with hydraulic lift and headlights, and a 14hp Kohler K-series engine. If you're only gonna have one to start with and want to mow, push, throw, till or plow, then all the correct attachments are readily available in PA and surrounding states. A model 1450 is very similar (next newer model 14hp) and I'd recommend it as well.
As for being "semi-classic", I have to say all IH Cub Cadets are classics, just some more than others. Every model has it's "little" issues to maintain, some are better than others. There are Gear Head nuts on here, and guys that are diehard Hydro nuts (like me). Since you're just starting out, I'd definitely go the Hydro route.
Good luck on your hunt.
Lucas (under edit) - on your PTO bearing and locking collar - you better get yourself a bigger hammer. Until you get that locking collar loose you ain't gonna move that bearing.
Hydro Harry
Old Cubs Never Die
(they just find another resting place)