Yep $250 in 1965 would now be worth $1800. Bit like the Stu Hamm example I guess. I've been told by quite a few top guys they don't want to be playing something rare and expensive because they want to be able to replace it quickly if something happens on the road. (Clapton once famously said he played a standard Strat he could replace locally in a hour if it went missing.)
As a pro, I get paid for playing and sounding good - not for spending a wad on high end equipment.