If you know which luthiers are extremely popular you can easily get more than you paid.
I think the internet is the great equalizer. The high end stuff like old Pensa Suhrs, Bernie Rico handmade pieces, original Valley Arts guitars, Andersons, Vigiers, Collings, and a few others have a small but extremely loyal following. But because the base is so small it can be a long time before unloading one at a good price compared to what one paid for it new or used.
It's kind of like the small but loyal followers of Jem guitars who are willing to pay top dollar for used examples where as the regular herd go for strats and Les Pauls from Musician's Friend and Guitar Center because other people use them. With Jemsite and a few others devoted to high end Ibanezes (and Jacksons, Deans, and other metal guitars), it may be very hard to match a player to a buyer. I would go here if I wanted to sell a Jem before eBay.
I know if I get a MIM strat or Epi Les Paul for $250 from the internet used, it's pretty easy to use it for as long as possible and then with no problem turn around and sell it for $250 no questions asked. I think the closest thing to a used guitar that retains 100% percent like that in the Ibanez world would be a nice RG for $250-$350 with nicely maintained trem.
To me a guitar is a tool and expendable but probably just as important to getting better for me besides practice, improvisation, and music theory is to play the same scale, fret size, neck thickness, and something to the point where my hands know where every note is. It's not as much if I go for a bolt-on neck with 25.5" inch scale or shorter neck with Gibson style appointments but more that I stick with one. A single guitar can be like a perfectly customized pair of Levi's to some players who gravitate to just one instrument or instrument type like Clapton with Blackie. The more I progress the less a high end model helps with its better frets, neck, etc. I want to get the the point, or in the direction, where I could sound good playing a nice guitar or a barn door with strings on it. I know a few players like that and Paul Gilbert is a great example mixing great stuff with cheap stuff and sounding amazing regardless.