Under 30 feet you can still trailer, still find a slip, and still overspend. The first-boat mistake is buying the payment and discovering the slip.
A sane starting point
- Pontoon: social, cheaper maintenance (3% of price in this model), happy on a trailer
- Bowrider: the default first runabout
- Bay boat: more fishing, still trailerable
- PWC: cheap to buy, spendy to keep as a percent of price (6% maintenance)
Stay off cabin cruisers until you have a real slip quote. Twin engines and wet storage move the monthly number faster than LOA.
Budget the outing, not the sticker
Set hours and outings honestly. Twenty days a year is a lot of Saturdays. If the cost per outing makes you wince, look at a club or a rental for a season and keep the down payment.
Use a state cost page so insurance and fuel start in the right neighborhood, then replace every override with a local quote before you sign.