If the wind isn't blowing too much from the beam you could try raising the main while in the slip - that depends on strength and ability to get out of the slip and steerage way going before you t-bone a boat or pier. Maybe you could raise the main to the second reef while at the pier.
I'd go with modifying the main with a set of slugs sized to fit the track; and run the halyard back to the cockpit. You also should work out a reefing system you can use while single handing that doesn't require leaving the cockpit - and that means the halyard has to be back there. If the main is old try looking for a place local to you that sells used J/24 sails - maybe you'll get lucky and find one in good shape with slugs, trade in your old to reduce costs.
As to docking, trade up on the outboard and get one with a true reverse, or at least one that swivels around to make reverse. Then try backing in - you get more control that way because you would center the rudder and drive and turn the boat via the outboard alone. Most places that repair and sell used outboards allow trade in values; so that will help.
Don't give up on the jib - not using it will increase weather helm making everything else that much more difficult. I can't tell where you sail out of - but places like Bacon's here in Annapolis have excellent choices in used autopilots, sails and other equipment for reasonable prices.
As SD said, stay on the boat. At a mininum, wear a PFD or at least an inflatible. I don't want to read about you in some 'sailor lost while single handing thread'.