First, love those genoa tracks on the cabin top, that'll get you some tight sheeting angles even if it looks like you could run into some interference with the shrouds.
On a small boat it is tough, because even with something like a tiller clutch and motoring, the bow will swing off in the wind.
All good ideas above and your diagram looks fine, and you will have to drill a couple holes. Instead of adding a block on the mast you can add a halyard organizer plate and add blocks as needed. The small one here will fit your tabernacle.
Or a turning block directly on the deck would work.
And adding slugs really helps a ton in raising the main and is pretty easy and inexpensive. Sailrite has a guide and on my 17' I used example #1 which is plastic slides and no grommets needed. Literally < $20 in materials even including a few spares (which you will want!).
Here is the guide: Slugs, Slides & Shackles - Selection, Installation and Positioning Instructions
You would normally use a sailstop and then you can prefeed your slugs at the dock and have them held above the gate. On my boat, couldn't find one where the threaded part of the stop was narrow enough to slide in the track. Another option is a mast gate which is very nice but is $50-60 if I recall but you can DIY one also.
For my boat I drilled a very small hole (3/32" I think) and use a cotter pin attached via some very small line through another small hole. Fairly common and you can't lose it. Drawback is that you have to drill a hole and there is some slight risk of tearing your sail but just round off the cotter pin end with a file.