Re: Mostly singlehanded...what lines should I run aft?
I don't think I would want to mess around with penetrating the deck into the cabin twice in order to run halyards internally. That is just asking for trouble both with water ingress and a serious PIA factor when it comes to removing and re-running halyards in future. Some manufacturers are now running the halyards in channels with removable covers on them which looks nice if it is well executed. At least that way you get the clean decks without penetrating into the cabin.
There really is not much more friction with the halyard lead aft. It makes 1 90deg turn at the base, and then deflects through the deck organizer. There is a bit more friction pulling the halyard through the closed spinlock clutch, but I can still hand-over-hand my sails to the masthead. If for some reason there is more friction, I can 2-hand it, with the clutch holding between pulls. If I have crew on board, I can go to the mast and jump the halyard, while someone tails from the pit. When I am hoisting the spinnaker, I can steer with the tiller between my legs while I hand-over-hand the chute up, and then grab the spin sheet, trim in, and I am sailing. That is infinitely more efficient than having to run up to the mast for the hoist, and then run back to the cockpit to trim and steer. There is way more potential for something to go wrong if you are forced to tie off the tiller or use an autohelm (which I don't have) and run around the boat.
1979 Santana 30 Tall Rig