Analog vs. CDP: A fair comparison?

Ok, in summary, I'm planning on selling my Cary 303/300 and taking the funds and buying a TT rig including Table, Arm & Cartridge. I'll worry about the phono stage, record cleaning machine, etc. later.

Assuming I get $2,500 from the CDP, will I be able to get a used rig that will at least match the sound quality? Assume also that I will have a phono stage budget of $1,000.

Rest of the system if Cary 300SEI.

Is this a fair comparison? Or, will the sound just be different (i.e. tubes vs ss).

thanx much
The largest cost for either format is not in equipment, but in music software. If you get rid of the Cary how will you listen to any of your CDs? How many albums do you have to play on your new turntable. There's no rule about the ratio of music to equipment costs, but I would hope that anyone with a system such as yours would have several hundreds (if not more) CD/albums. Your software collection should determine which format(s) you use.
I agree with the others when they wonder if you already own lps, how many cds you have now, etc. The availability of software (lps) is a tough one. If you've never owned a turntable before, I'd suggest holding on to your Cary and buying a budget TT combo pack--TT+phono preamp. You can get new packages for less that $500 and used--well take a look on audiogon. After a year you'll have a better feel for what you are getting with analogue. I like the sound of my old Thorens TT (with a gram slee preamp and cheap audio technica cart) but because of the selection available on cd, I don't think I'd ever trade in my digital equipment for a better analogue set up. Reading the mags about analogue certainly makes this a tempting proposition, but for me the reality of do it whole hog would be too bleak. Good luck whatever you decide!
A Record doctor cleaning kit, a decca brush and a zerostat should surfice as a start(about$100.) I would spend most of the budget on the cartridge/phono stage. Used Well Tempered Table/arm combo usually sells used for $1100. I like the Dynavector P-75 phono stage, very versatile, you can use the cartridge of your choice. This should sound better than the Cary. There are many bargain cartridges in your price range to choose from, maybe a Shelter 501,Audio Technice AT-33PTG from Japan, Benz, Lyra, Denon, Dynavector,etc.
I disagree on the software concerns--vinyl is very abundant and can be much cheaper than CDs as used--just make sure you have a good record cleaning machine in this case. As far as specialty heavyweight vinyl pressings, they don't cost any more than specialty gold/remastered/diamond studded rewhatevered CD pressings and sometimes less. I also think the benefits are greater but then, I've never owned a really super high end digital rig.

There are a few issues you should consider: is the music you want more, as, or less available on vinyl than digital? Are you willing to go through turntable setup and periodic maintenance? Like the others have already brought up, how big is your digital collection and how will you play them? I would think it would make more sense to add a vinyl rig to your current system rather than replace your digital outright--unless I'm missing something?

Also, be warned that vinyl is different--better or worse is entirely up to you. Some people like me don't mind some pops and click in older records, others seems to have minor coronaries over it. By nature, records are inconsistent. New domestic pressings in particular are often a bit warped and sometimes pressing techniques are hardly impressive. Vinyl can be a mixed bag. Compact discs are at least physically more consistent--mastering jobs are of course a different story. If you plan to buy new domestic vinyl pressings or poorly stored old "garage sale finds," I would recommend you figure some kind of record warp correction into the turntable rig you choose. There are several option: vacuum platter systems as with SOTA, periphery rings, or standalone record flatters (I have zero experience with machines that purport to flat records but they are out there). Also make sure you have a good record clamp.
I am not sure if you are aware that you cannot play vinyl directly thought the Cary without a phono amp. You have to budget that in.