Your set-up is hard to follow ...
Personally, my preference is to hoist the sails from the cockpit and make it a one-person job while the other person steers. I wasn't able to follow your set-up so I'll describe my preference (it's not clear why you have the ability to just hoist one halyard from the cockpit).
You also seem willing to put in the work but a lot of my preference depends upon your willingness to spend money on the hardware.
If you don't have two cabin-top winches, you should. If you have a winch or two on the mast, all the better for goodies like spinnakers and such. Your boat sounds very similar to mine so I am assuming you have 4 sheaves at the top of the mast (like the wheels of a car). With this configuration, you can have 2 internal halyards on one side and an external halyard going across two sheaves. The internal halyards exit the front for your head sail and the rear for your mainsail. The external halyard can be used fore or aft, depending on your desire. OR you can have four internal halyards with one for each sheave. I have the 1st set-up. If you only have an exit hole for one halyard, it won't hurt to add another ... you just have to buy the hardware and plan the location. If I want 4 internal halyards, I have to drill 2 more holes.
Ok, your internal halyards exit the mast near the base. To bring them back to the cockpit, you need blocks at the base of the mast and deck organizers outboard to run your lines aft to the winches. Install clutches for as many lines as you want to secure in front of the winches so that you can secure the lines when loaded and free up the winch on both sides. You don't want cleats on the cabin top for this function because they are typically mounted aft of the winch (I had them and removed them) where they secure only the line that is already on the winch. Once your halyard is secured with a cleat, your winch is useless. I use the winches for outhaul, vang, 2 reefs, 3 halyards, and cunningham. That's eight lines so I have 4 clutches and a winch for each side. I like having all lines leading to the cockpit. There is a reason for this ... on a small boat like ours, the cabin top is not a good place to stand. Bigger boats have much more room at the mast so you can feel more secure there. Ours is too small, so I like lines led to the cockpit.
To run these line to the cockpit from the base of the mast involves a number of blocks mounted in a variety of manners. It is too hard to explain so you'll have to use your imagination. The turning blocks mounted to the mast for the halyards are very expensive (2 came with the boat - 1 I had to purchase) so you have to weigh your priorities. The other blocks were not so bad. The deck organizers were simple, they are 2 stacked over 2 on each side and the new 4 sheave organizers fit the same footprint as my original 2 sheave organizers. Many people don't like mounting blocks on the cabin top at the mast ... you have to weigh-in on your own regarding that issue.
Ok now that I have explained the set-up, here is the application. With Sue motoring and steering, I raise the main and set it for close-haul sailing. Sue either continues to motor and falls off slightly or she cuts the engine and falls off a little more so we are sailing with just the main. I grab the sail bag and head for the bow (usually it's already there when we leave the mooring or slip). I hank on the sail from bottom to top and and leave it in a pile on the foredeck. I work the sheets throught the fairleads and set the leeward sheet around the cockpit winch and cleat it so that when I raise the sail it doesn't flog. The windward sheet is just led thru the fairlead and flaked near Sue's position at the stern (near the other cockpit winch).
Then I hoist the headsail. If there is a lot of wind, Sue has to pinch so that I can raise it without too much trouble. I only like to use the winch for the last few inches. When I singlehand, I basically use the same procedure except that I hank on the headsail before leaving the dock so that I don't have to go forward while underway. If I'm lucky, the hanks don't snag on the rigging components just above the stem, so I don't have to go forward, but 25% of the time I have to unsnag something so that is where you really have to be careful if alone (on Lake Superior, I would NEVER have the same cavalier attitude about going forward - we have very flat, WARM water so going in is a remote possibility and taking a swim is not a life-threatening issue). If my helm is reasonably balanced and I use bungees to secure the wheel, I can do all this without too much course adjustment while underway. I usually have the engine motoring until the headsail is up when singlehanding. If I did end up in the water, the boat would pretty rapidly head into turning tight circles, so swimming to the ladder would not be too much of a problem, probably more embarrassment than anything else.
I hank it from bottom to top so it isn't falling in my way as I work up the sail. If we have crew, I will have them set the sheets and the hoist the sail while I am hanking from top to bottom. This works reasonably well and it gives them something to do rather than just sitting in the cockpit.
My headsail halyard is on port side so I like to be on port tack when hoisting the headsail. By moving the traveler down, I don't have a problem with the boom being right over my head while hoisting. It's a simple routine that gets refined with practice.
BTW, I've never felt a need for a downhaul on the head sail. With a little practice, I just maneuver the boat so that when I release the clutch, it all falls on the deck instead of the water. I don't understand why there should be a need to drag the headsail down with a downhaul.
The photo shows the set-up on stbd side. Draping the halyard over the winch is a bad habit that I haven't broken.
BTW, I've noted before how similar your boat is to mine in size and weight so I felt like my experiences are particularly relevant.
