Beginner in Vinyl - How far should I go?

I'm full of questions these days, but...

My question is, how far should I go? I recently went on holiday in Europe and picked up a few vinyls for really cheap (Eagles, Simon & Garfunkel, Diana Ross & the Supremes), and I'd like to listen to them, but I'm not sure how far I should go into investing into a turntable.

How much difference is there between getting some fully-automatic Sony/Teac turntable with built in phono pre-amp and actually making a further step up to a manual turntable with separate phono pre-amp?

For example, I could:

1) Get the TEAC PA688 turntable with cartridge, phono pre-amp, already included for $79.88 off J&R;
2) Get a Project 1.2 turntable with Sumiko Phono Box and a cleaning kit for $500 from Needle Doctor; probably less if I go with something like Music Hall.

How much of a difference would there be in the sound? I've also heard that vinyls get worn out and sound a lot staler and less detailed, so perhaps I'd be better off just getting the TEAC (or any other el cheapo one - any recommendations?)

I guess how much I invest into buying vinyl records depends on how nice the sound is, and how durable it is as a medium.

I appreciate any recommendations on hardware, both ways. Thanks.