I've bought 2 used boats out of state. I live in Minnesota. My Larson Hampton 23' cuddy came from a suburb just north of Atlanta GA. My Searay came from Cincinatti. In both cases I did the inspection myself and then took the boat for a water test before handing over the cashiers check. I was looking specifically for a certain make/model. Limiting myself to what was available locally was not an option. I'll definitely look out of state again if I need to. There can be a risk with doing this but I was pretty confident that both boats were worth the trip after seeing pictures and of course asking the sellers lots of questions over the phone.
I towed both boats back home myself so can't comment on the shipping.
Larson made some nice cuddles if you plan to do some overnighting . Loved my 1995 220 Hampton. They replaced it with a 235 Hampton and then the 220 Cabrio. All 4 of those port windows opened with screens, plus the screened hatch and large cuddy entry gave that boat tons of ventilation and made it a great overnighter. Also had a separate head compartment. No sleeping over a toilet. Even had shore power with onboard battery charger, refrigerator, 5 gallon water system and alcohol/electric stove. That second picture is my first trip up to the Lake Superior. I added screens to camper canvas after for more ventilation.