Believe me, I know what you mean. Like almost any endeavor, 80% is readily attainable (reasonably priced), but once you get into the 90% and especially the upper 90's the cost of a little better gets kind of insane.
However, despite having some pretty nice gear, give me a pair of Philharmonic AA's or JBL LSR 305's with some good music and I am happy!
As TLSGuy puts it, sins of omission are better than sins of commission; I can live with a little loss of detail, a little loss of bass, and, to a lesser extent, loss of highs, and long as the sounds that are presented are clean and reasonably balanced.
You might consider the $600 3400 instead of the $900 4400. As I understand it the main difference is how many speakers it will manage. 5.2 or 7.2 and the 4400 would be a bit of a waste! The 3400 gets your Audyssey XT32, which is what most people are after!
However, I would also consider that it is not a bad idea to live with good, but not necessarily great speakers to mature your awareness of your preferences before committing to high dollar speakers. I am not convinced that "my best" speaker now is the same as "my best" speakers 10 years ago (when I allowed my audio addiction to resurface). Also check for audio clubs in your area. You know there are some great systems on your area. I am generally disappointed with VS forum, but they do have a thread dedicated to people willing to demo their system for others by location and speaker model:
https://www.avsforum.com/forum/89-speakers/1354492-i-ll-demo-my-speakers-other-enthusiasts-thread.html
If you are ever passing through Atlanta, take an extra day and I'd be happy to host you for some A-B comparisons!