OK. I'll bite. I took a quick skim through my maintenance log, and split the list into 3 (somewhat arbitrary) categories - Safety, Highly Recommended, and Nice-to-have. Here are each of those lists, in the order I did them (note that this is close to 8 years of off-and-on work). Many of these items are detailed in
my thread. I'm too lazy to go create separate links for all of them here.
== Safety ==
--Flares - I recommend an LED handheld for compliance, since you don't have to replace that every 18 months. You can carry pyrotechnic flares as well (they reportedly remain reliable long after the expiration; we carry a 12-gauge launcher and some handhelds, but I don't buy new ones every year)
--Trailer brake lights
--Fire extinguisher(s) and/or fire blanket
--CO and fuel-vapor detectors
--Gasoline tank tie-downs in cockpit
--Rechargeable spotlight (mainly intended for night usage, as you'd expect. Also used in fog - move the light around and / or shine it on the mast and sails to make your position clear. In case of fog, one kid gets the foghorn and the other the spotlight
--Jacklines
--Radar reflector
--Bilge pumps
--VHF (with AIS receiver; nice where we sail, but not essential)
--Stem reinforcement (kit from CD)
--Reinforced transom and rebedded motor mount
--Trailer tires (Load raging E)
--Transom scuppers
--Lifesling
--Keel winch, cable, turning ball, etc. (this would have been higher on the list if the cable hadn't been replaced soon before we bought her)
--Cockpit drain (flanged adapter + ball valve)
--Replaced chainplates (new design from CD)
--Replaced standing rigging (CD kit)
--Replaced trailer brakes
--Quick-release on swim ladder (for emergency access in the water)
--Through-bolted starboard bulkhead (marginally a safety item - mostly it's just to relieve the squeaking as it flexes against the liner)
== Highly Recommended ==
--Jib downhaul
--BBQ and stern-pulpit mount
--New gasoline tank
--Depth sounder (our original one failed)
--Spare fuel line (when one failed; I bought two)
--Topping lift
--LED strip lights in cabin
--Reefing lines
--Anchor + roller + rode
--LED running lights
--Nylon traveler control lines (as recommended by
@thinwater)
--Remote VHF microphone and speaker
--Bow eye backing block (starboard from CD - ~$8)
--Larger bow and stern cleats (nice for multiple lines)
--Midship cleats
--NMEA-Wifi bridge to share AIS from VHF with iPads
--Spreader boots
--Foam pads over chainstay bolts and other through-bolts in cabin roof. Saves some brain cells.
--Trailer-plug wiring at mast base (replacing unreliable through-deck connectors)
--Sealed leaks in cockpit pockets (leaking into cabin). And drilled drain holes into cockpit (so the pockets don't fill with water)
== Nice-to-have ==
--Bimini
--Windex
--Electrical refit w/solar and battery monitor
--USB and 12v power outlets
--Bulkhead compass (this one could go in safety, depending on the sailing you intend to do)
--Inflatable PFDs
--Ball-lock pins on table attachments, so the table is safe to lean on (and still easily removeable when converting to a bunk)
--Running backstay + tensioner
--All-line halyards (replacing line+wire)
--Cockpit tent
--Outhaul (later replaced with an internal cascade system in the boom)
--RudderCraft kick-up rudder (this was a safety item for us, as the stock rudder casting was highly corroded. But if yours is in good shape, it's a nice-to-have)
--Rope clutches
--Furling headsail
--Pump-out and vent for MSD porta-potty
--Replaced cockpit-locker latches
--Bowsprit and furling Code Zero (maybe our favorite upgrade, but I can't call it anything but a nice-to-have
--Double-ended main sheet
--New main sail
--Bimini upgrades
--Fruit hammock
--Handheld VHF (backup to main VHF and for use in dinghy and kayaks)
--Tachometer / hour meter on outboard
--Outboard charger wiring