From high end digital to beginners analog?

My son, who basically listens to mp3/ipod, bought a cheap turntable recently for his low end bedroom system. This intrigued me and greatly amused his friends! I have been thinking about a trying a relatively cheap turntable and phono stage for a few years now. Have not had one in 20 years.
Will a $2k to $4k turntable plus phono, new or used, be a waste in comparison to modern high end digital?
Has anyone had a recent dabble like this, and what where the results?
IMHO, digital provides better value, and the extra money would better be spent elsewhere.
10-14-11: Unsound
"IMHO, digital provides better value, and the extra money would better be spent elsewhere."

I agree, provided you're starting from scratch and don't have a bunch of records. If you have a bunch of records then it depends on things like how many you have, your budget, how much you like cleaning and setting up...
A friend listened to my modest analog front end and started talking about prices and buying a TT. I told him to not even think about it because he doesn't own any records. By the time he bought the hardware and then a decent collection, he could get a much better digital front end plus a lot of CDs Hi Rez downloads. A no-brainer IMO.
Given how individual everyone's experiences are, the only way to find out is to give it a try.

I have a music server with several thousand CDs on it, and it was my main listening source for years. You can't beat it for flexibility and fun, IMO, and the software has gotten so good that it adds back in a lot that LPs used to be able to lay claim to as advantages - for example, while you don't get liner notes, you can get album art up on a hi-res display, with integrated access to all sorts of information including, but not limited to, liner notes (or the equivalent thereof).

I bought a TT about 4 years ago, and I absolutely love it too. I'm convinced, though, that it all comes down to the specific recording - there are albums I have bought for $3 used that sound phenomenal, and others that I've bought new, full retail, that sound no better than a typical CD. The 45 RPM Jazz reissues from Music Matters sound like nothing I've ever heard before on a stereo.

Some of the best luck I've had is older LPs that were recorded back before high levels of compression were used. An old (used) Van Morrison or Jeff Beck album, easily had for $5, sounds far better than any version of the CD, even with remastering, etc.

Finally, the experience is different, too, and I like both. With the music server, I can change what's playing rapidly, or put it on shuffle play with any subset of the collection I want. With LPs, I'm more mindful about what I'm picking, and I listen to at least the whole side, if not the whole album. Both are great.

If you go the TT route, just be sure you are willing to take the time to set up the TT (or have it set up) properly, regardless of how much you spend on it. Great music on a well set up analog system, even a modest one, will be very satisfying.
I was in your position and I took the plunge. I bought a VPI Classic 1 and a Herron VTPH-2 phono stage the cartridge is a Benz Wood SL. I am extremely satisfied with the set-up. My CD player is a highly modded Sony SCD-1 and it can not compare to my analog set-up. I hardly ever turn it on anymore. I buy mostly new vinyl and have good luck doing so. I do pick up some used records from time to time and have had good experience with that as well.Would I ever go to an all analog setup NO. But the reality is digital just isn't there when compared to vinyl. For reference my Sony compared very well (side by side) to the AR cd reference 7 on cd only of course on SACD it bettered it. I say take the plunge.

Mike60, you have received a lot of great advice above. IMO it might take closer to the $4K number if you are looking for a table and phono pre. But who knows, there is a lot of good used stuff hiding out there.

When I jumped back into vinyl 7 years ago I used my old conrad jonson PF1 as the phono pre (using the ouput from the tape outs to the line stage). It may take a little more research finding and using a vintage preamp this way but it is an option to consider IMO.

I probably spent $5+K on my first vinyl system inculding a MC step up transforrmer but it was clear to me that it was better than my $7K CD player. On a few difficult recordings maybe not by much.

But I have gone way beyond that now and I am also much better at the TT/arm/cart set up. At this time vinyl playback just kills CD play back in my system. I suppose I could update my CD player but the red book CD standard is a limited format. There aren't any more bits to be pulled off those shiny disks.