I lived aboard a 22'' sloop for 4 months as a test to see if I liked it enough to do it permanently on a larger boat (the answer was a resounding YES)
1) The handiest item aboard was the VHF radio
; my sailing partner in his boat did not have one, and really wished he did. Used almost daily for weather reports, bridge openings, asking directions or advice, making dinner plans, finding fuel
and water, and confirming that the really big container ship behind you really *does* know youre there.
2) The single biggest hassel aboard was the dinghy
- a cheap inflatable meant for lakes and rivers - it towed poorly, even with the bow lifted in a sling, rowed even worse, motored well til the tiny electric motor broke, and had a tendency to turn over in high winds... one time in very high winds (25-30kt) it actually flew like a kite at the end of the painter.
3) Put a lot of thought into what you bring aboard. Assuming most coastal cruisers are around the 30'' range, youre going to have slightly more storage and living space than, say, a Volkswagen Bus. I packed everything I thought I might need into that boat, and never touched half of it. I think ''Sensible Cruising'' says it best; something like ''dont think about what you can live with, think about what you cant live without''.