I was in you shoes about two years ago ... all I can tell you is in my case it's been well worth the "journey". I say that because at first I just wanted an older vintage table with a basic cart and be done with it. We had a little "audiohead" gathering at a local pub and I asked the question "what table should I purchase?" I basically got my head ripped off for asking such a dumb question and never did get a straight answer. Every question I asked was answered by 3 more questions back to me. I continued on to my local used audio dealer and was given so my options I had found myself back at square one.
Here are some of the mistakes I made :
1. Dont underestimate the possibility you may stay in analog for a while and start buying LPs which could bring on the upgrade bug regardless.
2. Invest in a good LP cleaning system - I bought the Spin clean because it's inexpensive and seems to do a pretty good job.
3. If you pickup a turntable w/o a cart make sure the cart you purchase works with the turntable. Yes, I actually bought a cart that was such that the VTA on my turntable didnt accommodate it very well. The same goes with the cart and the phono pre - not all MC carts are created equal.
4. Space ... No, not a Deadhead interlude - LP's and cleaning systems take up a lot of it as well as the table itself. Just something to think about.
I like the Rega/Ortofon combo because it's been matched. I almost wished I would have gone that way but I have picked up a lot of knowledge about what I like along the way and I am still not into my analog setup nearly as deep as my digital setup. I find myself listening to entire LP's now where with digital I hop around a lot. I have rediscovered a lot of music I had long left behind which was an unexpected bonus. The sound is very pleasing but then again, so is the digital setup. Im glad I did it and I hope you are too.
Good luck,