Responses from sidssp

Turntable That Can Automatically Replay A Track?
If you want something high-end, you might want to look into The Laser Turnable. 
What's your favorite Apple-based music program?
Glad to know you like Audirvana. Since you are using Mountain Lion, make sure you try the latest beta In my system, on Mountain Lion, it sounds much than the release version 1.3.5. 
Which speakers should I get. $500-$1000
For jazz and classical, I suggest a pair of Vandersteen 2CE signature. They are smooth sounding, easy to drive and pretty full range. But at the end, audio is 100% subjective hobby and it is best if you can test them yourself to see if they meet y... 
What's your favorite Apple-based music program?
I have tried pretty much all the software players I can find for Mac and I have been a licensed PureMusic (I actually started with PureVinyl) user for years. But at this time I have to say the best sounding player is the Audirvana Plus, particular... 
Why does Computers - Amp - Speakers sound better?
What do you mean by "better"? Audio is a 100% subjective hobby. As long as you like the sound from computer "better", there is no need to ask why; just enjoy it. 
Help with computer...
Second Timrhu suggestion. 
Audio Research SP3A-1 or Conrad Johnson PV11
Bob, When SP3A first came out, it was considered to be less tubby than old-school tube and was described as "refreshing" at that time. If you like old-school tube sound, you might want to consider a vintage McIntosh C22 instead. 
What are your general thoughts of B&W speakers
I find them too dry to my taste but everyone's taste is different. You really should go by your own audition rather than others' taste. 
Silly turntable question
Some cartridges work better on long arm, some work better on short arm. It depends on what you have. 
HDtracks Music Libary Software For Macs
iTunes absolutely handles high res playback. It is the DAC and the interface to the DAC that limit how high resolution you can play. If you are talking about FLAC files downloaded from HDtracks, that is true, iTunes doesn't play FLAC. But you can ... 
Vandy 2W w/o crossover
Be careful how you ask Richard. He is approachable but he can be defensive and doesn't take criticism very well. 
Home stereo equalizer
For home theater application, you will be better off to use an AV processor with Audyssey room correction. They work much better than simple analog EQ. The one I like is the Marantz AV7005. I have set up a 5.1 system (AV7005 driving 5 Focal CMS50 ... 
What is the best vintage TT for new audiophile?
There are so many. Thorens, Technics, Denon mentioned by other posters are all good. I will also add Linn LP12 and Kenwood KD-500 or KD-550 (with arm). 
PC or Mac?
I think it comes down to what you enjoy more: listening to music or playing with computer. If you like the later more, you should get a PC. I used to work on PC all day in my day job and I didn't want to bother with it when I listen to music at ho... 
Which processor/preamp....
If you only want 2-channel, you don't even need a processor. Most TV has audio out. You can just connect that to your active speakers and you are done.