Want to upgrade turntable next year, upgrade path?

Hello everyone.  I'm a long time fan of vinyl but just recently bought a new integrated tube amp and speakers, and now realizing how good things can sound, I'm kind of hooked...shocked? haha.

Current setup:

Rogue Audio Cronus Magnum II  amp
Klipsch RP-600 bookshelf speakers
Technica SL-DD33 turntable
Blue Jean Audio interconnects
Chrome Cast Audio

I know there's probably a lot of things I need, subwoofer definitely being one, and maybe would be a better purchase prior to the turntable.   I also want to pick up a new DAC to use with the CCA. I've been looking at the Shiit Audio Modi Multibit. I've been looking at a new power cord as well for the Magnum II, as I've heard that it can make a difference. (skeptical on this! haha)

My budget for the turntable + tonearm + cartridge would be about $2000 .  I'm not opposed to used equipment at all. 

Assuming you have a Technics SL-D33 turntable now, I’d say you ought to look at a new turntable and phono stage first. Subwoofers are a dodgy proposition at best. Plan on upgrading your speakers after the turntable and phono stage. 

You need to to decide what functionality you want. In my case, I did not want a fully manual turntable, because I wanted automatic tonearm return at the end of play. That narrowed down the field considerably to vintage semi-automatic turntables. I bought a Technics SL-1700mk2 and restored it with a few upgrades including an Audio-Technica VM540ML. I upgraded my NAD PP2 phono with a Burson V6 Classic discrete op-amp and custom built regulated power supply. All in, I’ve invested about $1300 and I’m very pleased with the results. Hope this helps.