the cart or the horse?

I would like to agree with the excellent advice on upgrading your preamp / amp to as good a quality tube equipment as you can afford. I would invest in that first. Then, enjoy, save up and work on a good DAC… then upgrade your streamer. Then you can work on interconnects and cables.

Keep with the long game, 0ne step at a time. Luxman would be a good choice. An integrated tube preamp/amp… spend your whole budget… then save up for your next step.

Also, speaker positioning  can make a huge difference if you have latitude to move stuff.

I would suggest: a ps audio sprout 100 integrated to start with, get a pair of Revel M35 which are a smallish floorstanding speaker and get some decent cables. Use your streamer until you can afford a standalone dac/streamer like a used ps audio DS jr dac with a built in network card. I have this setup in my living and it sounds very nice.  

I ask this in all sincerity,  why  the recommendation to change the Omega monitor speakers? They are excellent and very efficient/easy to drive and a very good match for a 10x15 feet listening room. Different speakers but still saddled with the same amp and preamplifier. What is the driving rationale? Simply curious. 

Charles 

I agree with @charles1dad because you also like jazz at lower volumes.  A nice tube amp could put some meat on the bones and as he says you don't need to worry about spending a fortune or chasing tons of watts. 

But @jjss49 makes a great recommendation on that Hegel.  

Since you are open to moving step by step, I think you could tackle the amp/pre side first, keep those speakers, and then get a good DAC for the Bluesound at some point.  

Try your best not to get research fatigue.  Keep it fun. It's a journey.  Keep us posted. 

If you keep the omegas, which are great, stay away from amplifiers with high dampening. A quality set amp is the ticket.