newbie question- omega/meadowlark/traingle/reynaud

Hi. I used to use paradigm atom and 3se mkIII speakers for my old system. Now I'm thinking of upgrading my speakers but I've limited budget for each component.

My current system is:
NAD 521i CDP
Dared VP-20 tube amplifier with 18watts/ch
ASL LH-01 pre-amplifier (as headphone amplifier)
signal cable analog 2 IC
speaker cable borrowed from my brother (thus I don't know the brand)
mostly jazz/piano concerto/classical music

I am thinking of buying a pair of used speakers for about $500. I auditioned Triangle Titus and I quite like the sound. But I read from AA and here that Omega TSx speakers, Meadowlark Swift/Swallow and some others are good as well. Since I'm in an area that doesn't have a lot of audio shops, can you all recommend any speaker that's good for my application (and about $500 used)?

Also, the VP-20 has 12AX7 and 12AU7 pre-amp section, but it only has one input. My headphone amp (ASL LH-01) has 3 inputs and it would be nice if I can connect them together. Will they work well together?

any other suggestions will be appreciate as well.

Thanks.