Starting from scratch, passion for "steals"

For those who don’t like reading long posts:
I want recommendations on equipment, especially speakers, to keep on the lookout for that are SOLID performers for a dedicated 2channel system, that can be found for song (pennies on the dollar for performance equivalents). This opens up to vintage equipment, or more common equipment that can be found for cheap. I’ve got room for floor standing speakers and am not placement restricted, but I am limited with what I can do for sound treatments (baffles/foam etc) so keep that in mind. Jazz, Blues, Alternative, Folk, and some classical, is what will be mainly on this system.. (any of the harder stuff, trance, techno etc, will likely be handled by the HT system downstairs)

Now for those that like to read a stranger’s dribble and blather:

Ok, So as you can tell, I'm new here, and honestly I can’t claim to be an audiophile, as my technical knowledge is enough to know that I don’t really know enough, nor do I have the experience to make that claim. (as in my opinion, one has to be "familiar" with excellent equipment and music to reference what is good.)

Fortunately or rather, unfortunately, for me, though I dont have the technical knowledge and experience of an audiophile, my hearing is, well, as friends and family say, freakish to "unnatural". Now that doesn’t compare with a "trained" ear, but it does mean that I am typically disappointed in my or anyone else’s system, and forced to just make due.

Now, I sold a/v and HT for years in the mid 90s, went through all the training even getting what was the original THX certification for sales and design (useless btw) etc. etc. but the equipment we sold topped out at high consumer/very low high end.. goodguys btw so adcom/denon/polk/klipsch/energy were about as high as our stuff went. Good consumer stuff, but still a "box-store" so to speak. I'll admit that I was one of the more knowledgeable in the whole company when it came to home theater of that age, as I had just finished film school, but audio,.. pure audio,.. is a different beast altogether.

I finally have a home with room to set up a real system (actually more room/rooms than I know what to do with) and am ready to set something up that I can truly enjoy.

Unfortunately, in acquiring this home, and being in the process of almost completely remodeling it, now isnt the time for me to spend 10-40k for audio equipment. In fact many would say now isnt the time to buy anything.

Also I am afflicted with a condition where I just dont feel good about my purchases unless I'm getting something excellent for the price of something average or even less. This leaves me desiring those "hidden gems" and "crazy deals". But to get them in this arena,... I need patience, vigilance, and commitment, which I have, and expertise,.. which I dont have.

So I'm asking here for advice with regards especially to speakers... (as most of you will agree are possibly the most varying factor in a soundsystem)

I want advice on what speakers, vintage or modern, to be on the lookout for, that might fit someone like me. ( I know I’m not going to get Wilson Audio sound,.. or top of the line Martin Logans etc. as I have heard those setups, even though now I wish I hadn’t.. But, my current polk/denon (not either’s top of the line) never really satisfied, even though it was better than many. I’m looking for ideas, and advice from long timers with experience on the performers that don’t necessarily get the attention of the “price is no object” crowd.. Price is a big object right now. Maybe later I can upgrade a piece at a time, but starting from scratch.. It’s a bit overwhelming.. I think most of you have an idea where I’m coming from.

I will also throw in that I am leaning toward a tube amp setup as I, to this day, regret getting rid of my first hand-me-down system that my dad brought back from overseas when he was in the military before I was born. It was an old sansui 1000A which was supposedly a Japan only version, or so I remember that being the excuse for the cost of repair parts, with a TEAC real to real, cant remember phone, but the speakers had custom fabric for the grills so I never knew what they were, but I do remember that they weighed like 40-50lbs each.. Anyway, as taken for granted as that “old junk” was by me, I still yearn for the sound that came from it. Warmth just doesn’t seem to capture what I remember of it.. Although it did heat up quite a bit, and have a smell all its own.. Yeah, I miss that. (especially after just looking it up and seeing that people still like this guy.. I actually think I gave it away) Regardless, I doubt that even the exact thing would live up to the memory, but,. I do like the idea of a tube amp again, though I’m not stuck on it.

Anyway, thanks for reading and any advice you can throw my way.. If none, that’s fine too, I will just continue to scour the rest of the board.