From high end digital to beginners analog?

I have about 300 records that I just used to stare at, never play because my CDs via a Rega Apollo sounded much better than my bottom feeder analog.
To upgrade my analog I bought: Rega P3, Denon Dl-103r, Musical Surroundings Phonomena Nova, all used at under $1200, retail over $2K. New Apollo cost $1K. Just to give you an idea what level I'm talking about.
The analog now sounds a little better than the Apollo, I play both CDs and LPs and can enjoy either without wishing I was listening to the other format.
So I don't think you'd be wasting your money - Provided you already have records. I would not expect a $2K - $4K analog setup to blow away hi end digital, or even a digital front end that cost $2K - $4K for that matter.
The other thing with records that probably sounds cliche and overstated is the tactile experience.

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.