Nick:
I got back into vinyl about 6-7 years ago and here is the path I followed, and some recommendations.
TT: I started with a Rega-25, found an old but mint Thorens, and ended with a Teres 265. What I have concluded from that journey is (your experience may vary), the Rega had about 90% of the musical quality of the Thorens, which had +/- 95% of the musical quality of the Teres. If I remember right, the Rega cost about $1,200 with arm & cartridge, and the current set-up with arm & cartridge is +/- $10K. Or, for $9,000 you get 5%. Don't get me wrong, for me, the $9K was worth every penny!
Phono Pre-amp: Same as above, starting with Rega, to Coif Nia, to EAR, to Herron. $100 to +/- $3,500 for 5 to 10%.
Cartridge: Same as above. $250 to +/- $3,800 for 40 to 50% increase in musical quality. This and the speakers, are the only up-grades to my system (for either vinyl or digital), that really made such a huge jump in the quality of the end product (the music).
Cables, tweaks, amps, pre-amps, etc: All, and I mean ALL, up-grades have followed the same path with the same result. With good quality entry level equipment you will get 90 to 95% of what you can get. Getting closer to the audiofool goal will cost you big bucks, but it is really alot of fun!
So, what does a terminally broke audiofool recommend?
First and most importantly, shop around, take your time, and buy used, good quality equipment. The prices for new equipment are not worth paying, for an audition.
Second, tailor your system to your environment. If you live in a house or apartment with anything but a concrete slab for a floor, you need to understand that a TT with a suspended platter (Thorens, etc) will be hard to set-up so that the needle doesn't jump every time someone walks across the floor. It can be done, but it takes stands, tweeks, etc, which translates into unexpected $$'s. The solid TT's are easier to set-up on a suspended floor and the musical quality has much more to do with the cartridge than the turntable design.
Third and last, the speakers, the cartridge, and the media are what you will hear. Spend your money there at the start and modify the stuff in-between later.
If you take your time and shop wisely, you can get a 90 to 95% system (which by the way, is pretty damn nice!) for not much money.
As far a the vinyl is concerned, just make sure it is clean.
Best regards,
Dave