What should I upgrade first on my budget system?

To better answere your question more info is needed.

Have you optomized your room for playback?

Which Rotel CD player do you own? Does it have digital output?

Is there a priority betaeen vinyl and digital?

What is budget for upgrade?

op’s speakers

http://www.coincidentspeaker.com/dynamite-loudspeaker.html

The Preamp has very desirable features. I might consider it great value, inexpensive, but not cheap.

the tube amp appears well built, evidently maker has good reputation

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I’ll presume the speakers perform well in the space.

I would go for more power, to deal with instantaneous needs.

this is why using stereo amps that can be bridged as mono can be a good choice. Of course from a brand likely to be readily available.

Turntable: I do not like ANY of these turntables with tonearms that lack removable headshells. However, who knows, for some a single darn good cartridge, especially factory aligned might be best.

@coryb

Room treatments are pretty boring. They just hang on the wall and not much fun to play with. But, as other’s suggested, I’d make these the #1 priority in your upgrade plan to improve sound quality.

I’d hang a better cartridge on the end of the tonearm.

IF the Rotel has digital output(s), a good DAC will add rocket fuel to your physical media.

You mentioned you’re in Montana. Sorry, just couldn’t help myself and added this link.

Frank Zappa:  Moving to Montana

The right Cd/amp power cable upgrade can be as good as new component.

@digsmithd +1