Hi hamset,
I made the move to vinyl a year ago, and I don't regret it one bit. A few things you need to consider before taking the plunge, in no particular order:
The two main advantages of vinyl, to me, are 1) music savings if you have access to cheap used vinyl as
wnmnkh says, and 2) the ritual - nothing like sitting infront of the turntable with a glass of (insert favorite beverage here) and flipping records for hours...
Have a look at used record stores in your surroundings and see what prices and selection they have.
Also, in what condition is their stuff? No use having a good turntable is you can't find records in good condition.
Stay away from new vinyl unless you're a filthy rich hipster. Those things cost a fortune. Go for garage sales instead.
Many used record stores also sell used turntables which can be a steal compared to new ones of comparable quality - IF they are still in good condition.
Turntable setup isn't that hard to learn. Vinylengine.com is a great resource, they have manuals for any old pickup, tonearm or cartridge you will find.
Automatic is nice to have, but nothing's free. If you can live with a manual TT, you'll get more sound quality for your money. (And you get more of the ritual experience as well...)
Once you have a good TT, your sound quality depends on how well the previous owner treated their records. A clean record with no scratches will sound as good as digital. (I'm lucky because classical music collectors tend to be especially obsessive about record maintenance.)
My story: I started last year with a $150 entry-level Technics SL-20. After a couple of months I traded it in for an Ariston RD-11S which I upgraded with a JICO SAS needle, and fitted with new Linn springs. Total investment = around $750** after which I was satisfied with the sound quality. But since then, I have bought between 100 and 150 records at an average price of about $2. The savings have paid for the turntable in less than a year. (But somehow my wife doesn't see it that way... funny how saving can cost you money.)
** If you're not into classical music, you may need to spend less - classical is hard to render well because of the dynamic range (you hear the friction noise in the quiet passages, and the loud ones cause distorsion if your cartridge/needle can't stick to the groove so well). On the other hand, my old receiver already has a phono input so I didn't need to buy a phono stage. Your mileage may vary.
Good luck!