Moving from CD to analog

Absolutely agree. Audition as many systems as you can find. Then buy a table that would be upgradeable so that later you can add a better phonostage, and upgrade the tonearm and cart.
The guys with $16K systems have been listening to vinyl for years and have worked their way up to a dream system.

Why "change"? Just add a decent analog rig. These things are not mutually exclusive.

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.