re: First boat: Cal 2-27, Pearson 28 or Islander 28?
A couple of thoughts now that the boat is yours.
1. Icebox Drain. The drain from the ice box discharges through a small tube into the bilge. If you are like most of us, "stuff" will be spilled on the bottom of the box and eventually make it's way into the bilge drain. That can lead to some pretty unpleasing smells. And, the drain allows the cold air to bleed out of the box reducing it's usefulness. We solved these issues by carving a wine-bottle cork to fit the drain hole and plugging it and adding a layer of cut to shape "DriDeck" on the bottom of the box, sitting on a 1/4" layer of shaped closed cell foam. These can be lifted out and cleaned easily and the box cleaned out with a sponge. The closed cell foam improves the performance of the box. Also, depending upon where you live, many markets carry "dry-ice" in a little sub-zero freezer near the front of the store. These will keep the box quite cold and yet do not make a mess as they thaw as will water. As for Ice, keep a could on 1/2 gallon milk jugs. Thoroughly cleaned out these make good water bottles that can be frozen in advance, keeping the box cold and providing good drinking water to boot. I had planned to one-day add a refrigeration unit under the box--there is room--but found the foregoing arrangement sufficiently satisfactory that I never got around to it--in 26 years.
2. Engine Bilge Sump. The bilge sump under the motor is separated from the rest of the bilge which is good as drips of oil, fuel, etc. do not mix with bilge water and so are not discharged from the yacht when/if the bilge pump kicks on. I made up a "mobile" bilge pump, just a small submersible pump, that I attached to a 1"x2" piece of lumber and fitted with a 6' or so 1/2" diameter tube and powered by Alligator clamps that I could temporarily connect to the ships batteries. Sump water was pumped into a bucket with a POL absorbent pad that seemed to collect the vast majority of oil after which the pad was placed in a plastic bag for shore side disposal and the water tossed overboard. This seemed to work very well as we very rarely observed any "rainbows" on the water after dumping the discharge.
3. Chain-plate deck penetration covers. Keep a close eye on the chain-plate backings, particularly for the lowers. The deck plates are famous for leaking and the plates are mounted in positions where it it difficult to inspect the fastenings to the bulk-heads, but they must be inspected periodically and repaired as necessary. Crevice corrosion has been a problem with the chain-plates on these boats if they are not kept dry and clean which requires periodic replacement of the sealant under the deck plates.
Good luck with the new boat...
"It is not so much for its beauty that the sea makes a claim upon men's hearts, as for that subtle something, that quality of air, that emanation from the waves, that so wonderfully renews a weary spirit."