@CPC_1 I was in the same situation as you few years ago, found a great 1991 Prostar 190 in the middle of your price range in Michigan. There's not a ton of room in them like most inboards, but we squeeze 2 spotters on the front seat fairly often. Found it easiest to pull the back seat - more room for moving around.
I searched for only fiberglass stringers, so Malibus and Nautiques (mid 90s+) tended to be a little pricier than the MCs.
Maybe someone here has skied one to give some feedback, but the Supra TS6M kept coming up in my searches too, seemed like a solid ski boat at reasonable prices too