I have very cheap winter storage for my boats, but it still costs quite a lot to own and use them.

The 36' sailboat costs about $2,850 per year ($1,100 haul/launch step/unstep spars, $950 insurance, $300 mooring - town fee + maintenance, $300 dinghy dock, $100 oil change and winterizing, $100 tarps and frame maintenance).

The 32' powerboat is a bit cheaper at $2,350, ($400 haul/launch, $500 insurance, $1250 mooring rental, $100 oilchange and winterizing, $100 tarps and frame maintenance), but some of the difference is taken up by fuel costs.

A trailerable boat would be the ticket for cheap sailing, particularly if it was small enough to launch and rig relatively easily and quickly. My first boat was on a trailer and my costs were under $100 a year. It did take the better part of an hour to rig and launch it and about the same to haul and get it ready to trailer. Back then I sailed on weekends, so I launched Saturday morning, stayed at a marine state park or anchored out that night and hauled Sunday afternoon. The launch ramps were mostly free except when I used a state park ramp, which might have cost $2 round trip. A problem here in Maine is that there aren't a lot of trailerable boats WITH trailers for sale. There are lots of good boat ramps, but they don't get used all that much. Trailer boats are a good entry point, but these days everyone seems to want 30+ feet at the beginning. when I started sailing in my own boat, a 30 footer was a good sized family boat.

In contrast to the rosy picture Tom paints, mooring waiting lists here on Mount Desert Island, ME are years long and dinghy dock space it expensive if you can find it.

Personally, I would downsize to a 21'-26' day sailer if I could convince the Admiral, but keep the powerboat. There are two local builders that are putting out very nice boats in that size range, although they are a bit pricey ($55K+ for the 21' boat and $100K+ for th 26 footer). They are nice boats though