Moving from CD to analog

Generally, I would agree not to get started but with your budget and the quality of the system you already have I'd suggest two things.

Get ride of the CD player, rip your CDs and go computer based. You don't have to spend a great deal to get much better digital performance these days.

On the analog side a Clearaudio Performance turntable and a Benz Micro Ruby Z into an appropriate phono preamp.

You obviously agree with Rockport's take on sound. Why not ask him? He's been in high end a long time, he built turntables, and he certainly would want you to get the best sound possible from his speakers.

If possible, find a good dealer who sells several brands and have him set the table up in your home for you, together with a matching cartridge and phono pre-amp. IMO, you will save a lot of grief and you will have a resource to go back to for questions. A well-designed table, properly set up, should not require any maintenance for a couple of years. If you have absolutely no local dealer, I would purchase one of the better plug and play units from Music Hall or Rega. These are relatively easy to set up and will do a good job until you get more at ease with the process. If you buy from an online dealer like Music Direct, they can deliver the table all set up and walk you through any difficulties. I would still opt for the local dealer, but that's up to you. There are a lot of good tables out there and I would prefer one that is delivered and set up by an expert over another brand that I might like a little better for some reasons, but having to go it on my own.

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.