I do have a buying strategy, probably pretty weird. I buy guitars that I like; guitars that have the features I like; guitars that I can use on stage.
I like Strats, and the Legacy is the best Strat, with the features and upgrades that are the best for me. The other G&Ls I have give me other picksups--different tones yet the same ergonomics. I like Gibsons with bar tailpieces...SGs, LPs, 335s. I don't like trapeze tails; I don't like Bigsbys, especially the double-roller models. I need a guitar that sustains well. I prefer factory guitars over small unknown builds. There are more criteria, of course.
But, I leave all the weird, kinky guitars for Will Ray.
I've bought with an eye to investment, but I've stayed out of the vintage market...too many pitfalls, too many fakes and frauds. So I have a 52 guitar portfolio at the moment. Lots of dupes, many LPs and Legacys. Tried to buy low, with the aim of selling high...with the idea that trying to sell ten guitars and making $200 profit on each one is a better deal than risking $10k on a vintage guitar in a volatile market.
Of course, I'll probably die before I sell any! Lol! And I may want to take a couple with me!
Bill