Fascinating thread... and I'll state, that I've done this, now 3 times (4?)... You can infer my priorities by my work lists.
My Capri 25 (1982 masthead rig racing boat, outboard).
My order of "repairs" was:
- Bottom job (sand to gelcoat, barrier coat 5 coats, sand smooth, 5 coats VC17m)
- Outboard bracket (outboard was dragging in the water) new bracket caused outboard to clear water
- new halyards (less stretchy)
- new sails (all sails were dacron and 15+ years old)
- smaller outboard (6hp down to 2.2 hp)
- new running rigging
- upgraded vang from 4:1 to 6:1
- upgraded outhaul purchase from 4:1 to 8:1
- installed a boomkicker (removed weight of topping lift aloft)
- installed low profile genoa cars, installed inboard tracks for genoa
- upgraded backstay purchase from 4:1 to 8:1, pinch style backstay
- templated keel (before bottom job)
- templated rudder (before bottom job)
Best part is I did this all above over the winter season. It was like sailing different boat. I went from 13th of 25 boats to 2nd overall of 21 boats, in one racing season! Oh and my starts still stunk, so my boat handling was abysmal.
Next boat (my S2 7.9)... This was an outboard model fractional rigged retractable weighted daggerboard boat.
- Bottom was good, just quick smooth sanded, and applied VC17m
- installed new cleats for genoa sheets
- upgraded vang from 4:1 to 8:1
- internal outhaul was already 8:1, changed to loose foot main, for easier outhaul adjustment
- backstay was pinch style, I upgraded it to cascaded style, amsteel backstay (lighter) with 6:1 purchase, and controls split port and starboard
- upgraded to boomkicker, rigid vang would work too, this is a great light air upgrade, also handy.
- new mainsail (sails were mostly trashed on the boat, and on the fractional, the mainsail is your big power) couldn't afford new headsails yet, so mainsail first.
- low lead genoa cars installed (already had adjustable cars)
- main cunningham installed
- upgraded halyards to low stretch VPC (replaced every bit of running rigging)
- Installed velcro locks onto rigging turnbuckles (faster to remove and adjust)
- kept a log of rig tensions per race, including wind conditions, learned settings for each wind condition, applied them consistently using a loos tension gauge
- checked shape of rudder, and keel to class standards
- rerouted spin pole downhaul to mast base, for faster spinnaker adjustments
My present boat is a Wavelength 24, a fixed keel Masthead rig race boat (also outboard)
- First thing I did was quick sand the already smooth bottom, and apply 3 coats of VC17m
- Presently fixing the depth/knot meter, as speed over water is my most important "tool." both prior boats had very accurate (verified by GPS - we have no current ) knot meters. I am considering a speed puck too (GPS speed), my S2 had a VHF SOG GPS in the handheld.
- upgrading vang, and installing boomkicker
- replacing all the halyards with VPC or I may upgrade to endurabraid or MLX, I'm about 2 weeks away on this yet
- All the sails are recent vintage (some never used) racing laminate sails. I have full sets for the boat, including, Number 1, Number 3, main, and spinnaker (so at least 8 sails there) and a brand new used 1 time asymmetrical cruising spin, used once...
- Replaced aging motor mount (wood) with starboard and replaced aging 3.5 Nissan 2 stroke with Mercury 4 stroke that tilts clear of the water. I'm considering removal of outboard for racing and storing below.
- Removed all loose gear from below, and only adding back safety equipment.
- Will upgrade split backstay to cascaded before launch.
- Otherwise, boat already has sail controls missing on the other boats.
So basically from a cost perspective (because I do my own work), I start with bottom jobs first. Then sail adjustments, like adjustable cars for genoa, upgraded purchase for outhaul, vang, and backstay. Upgrade running rigging (especially halyards). Then I work on finer tuning stuff like rope clutches, cleats and such (for speed of trim changes) or I add them if they are missing. The easiest thing to make the boat faster is get all the stuff that drags in the water smooth or removed (fixed to folding props or in outboards get them out of the water)... Then other obvious stuff is to lighten the boat!
The pricey stuff to do but also the most dramatic is new sails! On a masthead rig, I'd focus on the genoa first (if you are primarily light air venue, number 1, if you consistently see 15 knots or better, then Number 2)... On a fractional rig I'd focus on a proper new main (loose foot is nice, get at least 1 reef point for when its howling). If dacron, make sure you have a cunningham (less necessary on laminate main). Outhaul, from cripes sake, make sure your outhaul is easy to adjust! You know ease in light, on in heavy (and all that). I can't tell you how many times I've lost my downwind leg because someone (me) forgot to ease outhaul downwind!
Upgrading running rigging helps lots (for making trim changes quick). Upgrading to low stretch halyards allows you to MARK the halyards (with a sharpie or a stitch), for optimum settings once you've found an optimum setting for a given condition.
I use a 3-2-1 rule (because we aren't hard core racers)... Everything has 3 settings for me... it makes it easier on the crew, and easier to convey settings for given conditions. There are of course exceptions... but
Outhaul starts as fully eased at 3, then moves to 2, then 1... genoa cars 3 light, 2 medium, 1 howling. etc... you get the point... if everything is numbered correctly for the crew, then they know Light air, medium air, and howling wind settings at a glance for each control. This gets you your "coarse" settings, and should get you to 90% of where you need to be, then you can fight for that last 10% under sail.
You asked I ranted.