Upgrade from my Planar 2

I was going to buy a VPI Classic, but my Rega dealer changed my mind (the VPI has a long wait list), and I bought a new Rega P5 plus power supply with a Benz Glider, so far new $ is (with a small discount $2,500 or so. Used P5 even better, and then you could get a Fosgate Signature Phono preamp.
If I was you, I'd get the Phono first, and look at the Fosgate, and at some other $2 grand ones. Graham-slee Herron VTPH (used here, now) you just missed Cary phono for $1,400
I'd get a great phono first and try it with the current TT and cart.
Then maybe even go for 1K cart and put on current TT until find a great used TT
Good 1K carts:
Benz Glider, Dynavector 17D3, Lyra Dorian, Shelter 501 mkII
MY stuff: Rega P5/Benz Glider with Bryston BP1.5
And Kuzma Stabi S/Sogi S with Dynavector Karat 17D3 and an Audio Research SP-15 used just for phono input
(I would like to get a Fosgate...)
Buy the phono first if you feel confused. And spend a good amount on it. You have good stuff upward of the phono, so get a good one you can keep. especially if you like the Tt you have and want more, A phono may give you more all by itself, second would be a Cart (even if it costs to mount it on current TT.
This isn't what you asked exactly, but it is my two cents..

I would agree with you (original poster). If I were shopping in that price range I'd look long and hard at the vpi classic. I'd match it to a dynavector 20x and spend the remainder on a good used phono stage (sorry, can't help you much there as I'm not really familiar with what's around in phono stages right now).

I'd also consider a used Michell Gyro with perhaps an SME 309 arm.

Elizabeth,
Lots of good thoughts in you post. After reading it, upgrading the phono pre first makes sense since my current table has a fresh calibration and cart. I prefer using tried and true combo's since I an new to the analog game. What cartridge for 1k or less would be the best match for the Fosgate?

Elizabeth,
Sorry I see you listed the Cart in your 1st response, Thanks