I am making some notes on each item for you...here's the 5 month winter plan in no apparent order, but critical/most difficult items first (keel for example), after reading 7 years of excellent forum threads...open to suggestions...
Mastup (buy or build), usually more cost effective to just buy a new one than the time invested in making one. Try to find a used one if possible. If you are welder you can make one pretty cheap with scrap material.
Keel refurbish; your keel looks pretty good but your pics are at a distance. Having your Pole Barn and Tractor puts you at a huge advantage. This is the best investment you can make in ensuring a long life for your keel.
Keel kit from CD; you mean the hardware like keel hangers and pin or the centering kit? hardware, yes, centering kit, no... You can make better spacers out scrap glass matt/cloth and epoxy.
Bottom paint; just choose one that is good for your waters but also does not degrade in open air and is hard enough to withstand the trailer bunks (so a soft ablative is not a good choice)
Hull – sand/compound/buff/wax; yes! Got a compressor with a big tank? DA sanders are air hogs. If you don't have a DA sander buy a reasonably priced one, you only need 400 and 600 grit wet paper, but going the extra mile with 800 or even to 1000 is overkill but might have super results if you have the time to do all hat sanding.
Replace all running rigging; in the spring, usually before or on Memorial day weekend, West Marine Does a 40% off bulk rope sale. get on the email list for sales flyers. Do the same for Defender.com, they have good everyday prices and sale prices too.
Run all lines aft; my thread has lots of info on this, it will have more as I get to rigging my boat. Keep in mind you might have to loose the hand-rails to make room for the lines.
Tiller tamer
Replace standing rigging as necessary; again, I'll have more info on this if you want to go with Dyneema. Stingy Sailor has a good article about wire rigging on his blog/website.
Upgrade seal chainplates; The new style CD chainplates with welded collars, yes... They are really good.
Re-bed all deck hdwr; Get Butyl Tape from Mainsail's website.
Replace/reinforce bow eye; get the new one from Catalina Direct, the bow shield is a nice addition but not required.
Upgrade rudder gudgeons & pintels
Add midships cleats
Install mastgates
Topping lift you can also try a Boom Kicker or a rigid Vang. JMO, a topping lift adds too much crap to the end of the boom and all rigging in general.
Move/upgrade electrical panel; My thread has an example of this. There are simpler methods of installation, but install in that general area.
Add depth finder/compass/radio; watch for sales and rebates on VHF radios. I got a $40 rebate when I got my Standard Horizon VHF. Lots of slightly used handhelds on eBay.
Replace canvas (poptop/companionway); keep an eye on Craigslist for used industrial type sewing machine. I got a German made machine that is all metal, no plastic for less than $200. Learn to sew, it will save you hundreds if not thousands over your boating lifetime.
Replace poptop mechanism w/gas shocks; Stingy Sailor has an article on the horizon about this, read that when it comes out before you by the CD kit. I hope I just didn't give away any classified info!
Isolate/vent gas tank locker; this is hard to do and not totally necessary. Making a divider is easy, making fit it the area you intend to isolate is a royal pain.... trust me. When you stick your head below in the port cockpit seat you will understand why. My solution is to place my 3 gallon tank under the tiller. No one really should have their feet there anyway.
Fabricate mini-galley of some sort for Admiral
Table rebuild
Replace lights w/LED’s, rewire as necessary; good idea... See Stingy Sailor article on LED strip lights.
Refinish exterior teak. I got rid of all my teak, went to white plastic. You gotta love teak and varnishing if you want to keep up with it.
Install pushpit rail magma grille