Bigger Boat Recommendations?

[SkunkBoat]

you listed a lot of big inboard & I/O boats. The Searays are a nice family cruiser but nobody would mistake them for a fishing boat. The Tiara and pursuit expresses are sweet.
Once you get over 25' and/or 8'6" wide, trailering is another level.
You need twins over 25' too. Thats another level..$$$.

I went up to a Grady 265 express. Love it.
Grady Gulfstream is a sweet WIDE 23'. Seafarer is in your range too.

I would suggest getting something that already has a hardtop and enclosure. Its a real bargain over adding one later...

23 & 25 Coastals fit the bill. Watch for soft decks and transoms.

when you are looking at 80's-90's boats they should be cheap. Probably overdue for a repower if they are nice enough to be worth a repower.

From a buyer's perspective, I would value an old 2 stroke at $0