FYI here's my sailboat inspection / maintenance mega-list [MS Word table format didn't survive the upload]:

Inspection Maintenance
Deck clean, uncluttered Non-slip wax
Deck core de-lamination, water penetration – flex , oil-canning, blisters Fiberglass rebuild if serious
Cleats / cam cleats corrosion, leaks, alignment Remove, clean, replace
Chainplates corrosion, leaks, alignment Remove, clean, replace
Pulpit corrosion, leaks, alignment Remove, clean, replace
Mast towing hardware corrosion, leaks, alignment Remove, clean, replace
Pushpit corrosion, leaks, alignment Remove, clean, replace
Mast towing hardware corrosion, leaks, alignment Remove, clean, replace
Stanchions corrosion, leaks, alignment Remove, clean, replace
Fairleads corrosion, leaks, alignment Remove, clean, replace
Winches corrosion, leaks, alignment Open, service, lube, replace
Rails corrosion, leaks, alignment, pins and retaining rings Remove, clean, replace
Lifelines corrosion, leaks, alignment, pins and retaining rings, tension Remove, clean, replace, re-tension
Forestay(s) fish hooks, chafing, alignment, pins and retaining rings, attachments Remove, clean, replace, re-tension
Backstay fish hooks, chafing, alignment, pins and retaining rings, attachments Remove, clean, replace, re-tension
Upper shrouds fish hooks, chafing, alignment, pins and retaining rings, attachments Remove, clean, replace, re-tension
Lower shrouds fish hooks, chafing, alignment, pins and retaining rings, attachments Remove, clean, replace, re-tension
Blocks / pulleys / travelers / alignment hardware straight, even, corrosion, damage, wear, alignment, pins and retaining rings Remove, clean, replace, re-tension
Rope halyards chafing Remove, replace, re-tension
Rope-wire connections damage Remove, replace, re-tension
Wood trim UV damage, fasteners Oil, re-fasten, replace
Mast crutch UV damage, fasteners Oil, re-fasten, replace
Windows sealed, fasteners, clean, leaks Remove, clean, re-caulk, re-fasten
Zincs wear Remove, replace
Rub rails straight, fastened, damage, leaks Remove, inspect, re-caulk, replace
Anti-fouling paint Holidays, scrapes touch-up
Hatches leaks, cracks, seals, clamps Remove, or replace
Lockers leaks, cracks, seals, clamps Remove, inspect, repair or replace
Lazarette leaks, cracks, seals, clamps Remove, inspect, repair or replace
Transom leaks, cracks inspect, repair
Mast straight, even, corrosion, damage, wear Clean, re-tension, repair or replace
Mast light wire and deck socket Corrosion, damage Clean, service, repair or replace
Mast hinge Corrosion, damage Clean, service, repair or replace
Mast hinge pin / pivot pin – lock nut Corrosion, damage Clean, service, repair or replace
Spreaders straight, corrosion, damage, wear, attached to shroud line, end protection Clean, service, repair or replace
Boom straight, corrosion, damage, wear Clean, service, repair or replace
Mainsail cleat straight, corrosion, damage, wear Clean, service, repair or replace
Connection to mast corrosion, damage, wear Clean, service, repair or replace
Boom vang Cracks, alignment Clean, service, repair or replace
Poles straight, , corrosion, damage, wear Clean, service, repair or replace
Sail tracks fasteners present, secure, leaks Clean, service, repair or replace
Welds Cracks, corrosion, leaks Clean, inspect, repair or replace
Navigation lights Work, damage, dirty Clean, repair or replace
Bumpers Damaged, dirty Clean, repair or replace
Dock lines Chafing, dirty Clean, repair or replace
Canvas
Dodgers Chafing, dirty, worn Clean, service, repair or replace
Biminis Chafing, dirty, worn Clean, service, repair or replace
Equipment covers Chafing, dirty, worn Clean, service, repair or replace
Pop-top cover Chafing, dirty, worn Clean, service, repair or replace
Cabin
Floor damage, leaks Clean, service, repair or replace
Ceiling liner damage, leaks Clean, service, repair or replace
Bulkheads / dividers not shifted at connections to deck hull, or ceiling liner, water damage Secure, repair or replace
Galley
Pipes work, leaks, clamps repair or replace
electrical wiring Work, secure Repair or replace
fuel tanks Work, full, secure Fill, Repair or replace
pumps Work, leaks Repair or replace
Dinette Secure, damage Repair or replace
Water tanks Leaks, secure Repair or replace
Dry storage Secure, damage Repair or replace
lights Work, corrosion Repair or replace
Berths Clean, service, repair
Storage areas Dry, secure Clean, service, repair
Lights Work, corrosion Clean, service, repair or replace
Bilge Oil, debris clean
Pumps operational, leaks Repair or replace, tighten clamps
Limber holes debris clear
Hull
Blisters Drain, inspect if water in laminate Remove, repair, restore gel coat
Cracks Inspect if beyond gel coat Fill, restore gel coat
Scratches Inspect if beyond gel coat restore gel coat
Impact damage Inspect if beyond gel coat restore gel coat
Thru-hull fittings corrosion, leaks double clamps, lube seacocks
Cockpit drains Drains, leaks
Outboard well Drains, leaks
Water ballast valve Leaks, corrosion Clean, replace gaskets, hardware
Pop-top
Locking devices alignment, functions Repair or replace
Seal straight, flexible, continuous Repair or replace
Forward hatch
Locking clamp alignment, functions Repair or replace
Seal straight, flexible, continuous Repair or replace
Cabin hatches
Seal straight, flexible, continuous Repair or replace
Keel / centerboard Damage – leading edge Repair or replace
Lock pin / pivot pin alignment, corrosion, damage, wear Repair or replace
Uphaul hardware alignment, corrosion, damage, wear Repair or replace
Rudder Repair or replace
Blade damage, leading edge Repair or replace
Hinges, pintels damage, distortion, fit, guide holes round not oblong Lube, repair or replace e,
Pivot bolt and nut damage, distortion, fit, guide holes round not oblong Lube, repair or replace
Tiller blisters, de-lamination, damage, distortion Repair or replace
Engine
Spark plugs Present, working Clean, replace
zincs wear Replace
impeller works Replace
primer bulb Works, leaks Clean, repair or replace
fuel line Works, leaks Clean, repair or replace
Fuel tank Clean, leaks, gauges, Clean, fill, repair or replace
oil Clean, full Replace
oil filter Works, leaks repair or replace
fuel filter Works, leaks repair or replace
Propellers bent, nicked, notched, cracked Replace
Backfire flame control device present replace
Safety cable sound repair or replace
Clamps Tight, lock, motor solid replace
Papers
Title Match to hull numbers Inquiry, report, no-go
Insurance Match to hull numbers Inquiry, report, no-go
Registration Match to hull numbers Inquiry, report, no-go
HIN Match to trailer registration Inquiry, report, no-go
manufacturer plate Match to trailer registration Inquiry, report, no-go
Coast Guard required equipment
PFDs inspect replace as needed
Fire extinguishers inspect, check expiration date replace as needed
Flares inspect, check expiration date replace as needed
Air Horn / hailer inspect Repair or replace
Nav lights inspect Repair or replace
Dinghy / life raft inspect Repair or replace
Placards : oil discharge, waste disposal Repair or replace
Other
Anchors inspect Repair or replace
Anchor rode[s], chain, connectors inspect Repair or replace
Sea anchor inspect Repair or replace
Series drogue inspect Repair or replace
Rocker stopper inspect Repair or replace
Jack lines inspect Repair or replace
Safety harness(es) inspect Repair or replace
Man overboard float, flag, rescue rope inspect Repair or replace
Radar reflector inspect Repair or replace
Mast float inspect Repair or replace
At-anchor lights inspect Repair or replace
Electrical
Batteries water level if not sealed, terminals, terminal covers clean & lube
Lights test, spare bulbs, corrosion Repair or replace
Gauges test Repair or replace
Shore power check line, inverter, sockets, Repair or replace
fuses and breakers inspect Replace as needed
Connections Corrosion, shrink wrapped, copper Clean, replace as needed
Wires neat, organized, labeled Repair or replace
Electronics
Radio check, spare batteries, check antenna Repair or replace
GPS check, spare batteries, check antenna Repair or replace
Sonar check Repair or replace
Radar check Repair or replace
Compass check calibrate
Nav check charts / tide book / nav tools / logbook / radio channel list replace
Head working, chemicals and TP at hand clean, lube, treat, replace
Trailer
rollers and pads Worn, loose Repair or replace
wheel bearings Check lubricate
winch Check Clean and lubricate
winch pawl / latch Check Clean and lubricate
winch strap Check Clean and lubricate
safety chain from boat to trailer Check Clean and lubricate
tongue jack Check Clean and lubricate
lights Check Clean and lubricate
electrical connection Check Clean and lubricate
tires pressure and condition Inflate, service
wheels lug nuts Tighten, replace
brakes breakaway chains Repair or replace
tongue lock works Repair or replace
Boat on trailer Level, tongue weight Adjust
Mainsail clean, stiff, wear / chafing Repair or replace
Main halyard Bowline through twist pin U shackle, pins and retaining rings Repair or replace
Roller / furler gear wear, damage, drum, stay couplings Repair or replace
Reef points wear, damage Repair or replace
Attachment hardware wear, damage Repair or replace
Batten pockets - wear, damage Repair or replace
Battens wear, damage Repair or replace
Stitching – seams, wear, damage Repair or replace
Jib clean, stiff, wear / chafing Repair or replace
Jib halyard Bowline through twist pin U shackle, pins and retaining rings Repair or replace
Roller / furler gear wear, damage, tape, drum, stay couplings Repair or replace
Attachment hardware wear, damage Repair or replace
Stitching – seams wear, damage Repair or replace
Genoa clean, stiff, wear / chafing Repair or replace
Genoahalyard Bowline through twist pin U shackle, pins and retaining rings Repair or replace
Roller / furler gear wear, damage, tape, drum, stay couplings Repair or replace
Attachment hardware wear, damage Repair or replace
Stitching – seams wear, damage Repair or replace