Sorry to be a kill-joy, but I've been caught by this on a PRS singlecut - I didn't save a penny really, and it was a real drag as well...
The Tyler/Suhr etc boutique end of the market are generally guitars built just for you, the resale value isn't the same. You'll have to go for the mass market models as an investment really. PRS might be a good bet - they retire models very frequently.
I buy old Ibanez guitars, which seem to go up in value but I but them because I like them. I bought a 1977 Les Paul Pro a while back because that's the year of my birth. Time will tell if it was a nice investment or not, but it's a nice guitar. If you buy a guitar as an investment you'll want to keep it mint. Are you a player or a collector?
If you want to play it, don't worry about anything but what it plays like....
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