@grislybutter - they're not $10 records you're comparing them to. They're $20-$25 records if new. If they are 45's they are more. The One Steps are mainly 45's and they are $125. The 33s are $100. Compare apples to apples....
I avoid used records at all costs because you don't know what you are getting, although I am sure there are some bargains available. I've been able to pick up some NEW records on eBay for $12-$15.
The One Steps have already gone down a bit on Discogs, some titles more than others. I hope it continues.
Usually record stores price their used records based on condition (or maybe how much they paid for it, which should be based on condition), so the more you pay, the better SQ you get.
In terms of getting "the most" out of a record, that is impossible to assess. I would say more like the value, which is in the eye of the consumer. My cousin has a couple thousand dollar system that he thinks is very good and has other priorities than upgrading it (and that is really all that matters) and he appreciates better sounding records and buys them sometimes. I consider my low 5 figure system beyond very good (and don't want to invest a lot more - I've built it incrementally over 40+ years, never in big chunks) but plenty of people spend high five into 6 figures, some even 7! If you're playing with Monopoly money, why not? It must be nice. I just hope those people have the room acoustics to justify it. My brother in law has spent probably $60K or more on his system and it is in his office! (maybe 10x12) with speakers close to the wall because he can't move them out due to space limitations.