Speakers - Your "Safest" Choice

Focal Kanta 3, Revel 328 Be, both easy to enjoy and comfortably under $20K.  
These I know, and are “conventional” types. Ohm Walsh 5000 or Magnepan MG 20.7 are choices for certain types of rooms and listeners. 

I would never spend $20k on a pair of speakers BUT if I had to, I’d get the Alta Audio Adam for $17k. I heard both pairs at AXPONIA last year and again this year too (I think). What I WOULD do if I had $10k to spend, is buy the Tekton Moab AND Claytion Shaw’s new Caladian open baffle design and I’d still have lunch money left over.

A pair of OG JM Lab/Focal Mezzo Utopia's. 

How about a pretty economical trip to the Florida expo in February. (For me about $800, flights, hotel, tickets to the event, 1 free for my beloved…) then go talk to madman Greg of Volti Audio, have a listen to what he brought to the show. After a good listen there, head to other rooms and compare. I’m fairly confident you’ll head back to see Greg. His passion is infectious, his creations are amazing. Yes you can call me a devoted fan, or fanatic… but I’d put my Volti Razz up against anything south of $20k, they are that good to my ears.

I can't picture a trip to NY for a "few days" including airfare, hotel, transportation and food for under 5 K

Drive (if you're close enough); then if you happen to find speakers you really like, you can take them back with you (and save on shipping).

Don't stay in Manhattan. NJ, maybe. Look for unpopular dates and for deals. Even in Manhattan, you could stay in a Pod for ~ $120/night (incl. taxes & fees).

Eat street food (or bring something along).  You should be able to get a panful of rice rolls in Chinatown for < $5. Big Tray Chicken at Spicy Village (Chinatown) < $20, enough for 2. 

I would think you could have an enjoyable experience for about $250/day. Frugal, but not spartan.