My jazz collection told me to get a *real* system

The Bay area is one of the best places to be able to actually listen to potential purchases, and if you're willing to drive up to Portland, you can expand that experience. I love jazz with the right headphones, with the right speakers, with the right amp, but once one thing isn't doing it, I do not love jazz. I'm a digital source guy mostly and can't comment on your source, but I'd spend some time with speakers, and if a shop agrees - make an appointment and bring your own amp in! 

It might even be worthwhile to, wherever appropriate, make a post about your intentions and see if locals would be willing to invite you over to share their systems. We all know we'd love to have someone care about the little details. 

Thanks, willsw. I'm still a somewhat new transplant from Chicago and I have no idea how to go about finding audiophile and jazz kin. I'd love to find some folks willing to show off their gear. I'd be happy to bring some vinyl.

I would echo considering a tube preamp but, then again, I have a lot of tubes in my system (phono stage, preamp, and monoblocks).

The problem with used is that until you have listened to a LOT of different brands, you are really buying stuff blind (or deaf...). Reading other people's opinions is of limited use as we all 'hear' (i.e. interpret music) differently. 

Building a synergistic system (i.e. where all the components compliment one another) is an art. 

Finding kindred spirits can be done by posting notices on forums such as this one, or reaching out to any local jazz societies.

Good luck in your journey. And remember - it's all about the music, not the gear. 

And having fun!

I'd like to support Charles' argument: take some time first to find what approach works for you. It could be low-powered tubes and sensitive speakers. It could be big class A solid state amps driving panels. It could be classic Brit-fi. Go to some shows. Visit some bricks and mortar dealers. A good one will listen to you and lay out some options at various price points, including for the all-at-once vs one-"lifetime"-component-at-a-time-over-several-years strategies. 

My my own example: I heard a demonstration by Jeffrey Catalano of High Water Sound (dealer in NYC) at a show a few years back and couldn't forget the experience. Here at last was my sound. But way over my budget. I continued to try other components, but without feeling I was making any progress. Eventually I decided to give Jeffrey a call and just ask him: I can't afford that system, but how close can I get with a much smaller budget? I'm so glad I made that call -- we worked out a plan for  system that I love, I've bought three components from him so far, and I'm quite sure I will end up saving a lot of money over the long run.

And finally, enjoy the ride!

pingvin, out of curiosity, what was that "your sound" system that you heard at the show? High Water Sound deals in esoteric gear.