Moving from CD to analog

A couple of ways you can do this. Buy a lesser, but upgradeable table or buy a great table to start with. For the first option, you could go with a Sota Star, which is built in America and can be upgraded or traded in to a Cosmos IV, a great table. Same can be said for a VPI Classic to Classic 3 or Basis 2001 to 2500. For an arm, I would get the best I could afford, amongst SME 5, Triplanar, Graham Phantom or Basis Vector 4. There are plenty of great cartridges in the $2000 range, Dynavector, Lyra, Ortofon. Read a few reviews to see what meets your preferences.
As for a phono preamp, you will need to decide between tube or SS. The Manley Steelhead is well known, is excellent, tubed, and is very versatile, having remote control, 3 phono and one line input, variable output and many loading and gain options. It would be suitable with whatever table you end up with and can be used as a stand alone analog system without separate preamp.

If you decide to go with a top table to start with, the recommendations above will work, along with numerous others in the under $10K range. After that level, I think the differences are just that, not necessarily better, but different, and more to your preference than any real improvement.
It's nice to be able to put that kind of investment into an analog system

Been into analog since that was all we had. Do yourself a favor. If you really want to come to this dark side, don't waste your time on any of those entry level tables unless you buy used. Don't waste your money on any of those stratospherically priced things either. That time may come after you find yourself truly dedicated to getting the most possible from Analog. Look at the overachievers in the mid priced arena. I would be looking at Well Tempered, Nottingham, Merrill Replica, Kuzma, Wilson Benesche, Acoustic Signature, etc. Everyone else here would add VPI to that list, but I have no experience with them.

Getting rid of your CDs seems silly unless you're really "storage space challenged." Ever have a computer crash? Do you absolutely trust a NAS device? My NAS developed issues, I still have my CDs. Your CDs are their own best backup. also, I bought a lightly used Linn/Akito rig for peanuts, upgraded the cable, got a well regarded but inexpensive phono pre...and it sounds truly GREAT. 16K allows hundreds of options though, and you could wind up with your last rig.

Get a Basis 2200 signature with a Basis Vector arm, Shelter cartridge. The Basis line is upgradable and their midrange table/arm combination is great. Select a phono preamp, get a record cleaner, buy some records and you are good to go.

Personally I would not be too hasty getting rid of the CD setup. I recently added a TT and it is fun but also quite a bit of work. Putting aside the whole nontrivial issue of getting things dialed in, you have to jump up every 20 minutes to flip/change the record, which entails cleaning record and stylus, putting the old back in jacket, pulling the new one out, etc...in other words it is quite labor intensive for long listening sessions. Many people do not mind this (I don't either usually) but I have found that I enjoy both depending on the mood and have been listening almost exclusively to CDs lately. I also listen to internet radio, FM, and digital downloads, to me all formats have their virtues.