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'.
Believe it or not, I visualize leaving the slip under sail, but I'm nowhere near confident enough to try it yet. This motor does rotate for reverse, which has some fun side effects, like dragging the fuel line out behind the motor if you turn it the wrong way
. As I get more comfy I think I can live with the rotation, just my first couple of times were hectic.
The main halyard does run to the cockpit, which right now makes the operation slower, because when the boltrope jams, I have to run up to the mast, unjam, run back to the clutch and haul some more. Well, when I say run, it's only a couple steps, but still
I haven't called around about adding slugs or swapping sails, but probably will soon.
I'll keep using the jib, I just gave up for that day to let the steam vent and because messing around with it was taking concentration from everything else going on in the eyes of a first timer. I tend to focus on problems until they are solved, to the exclusion of other things... so I chose to forget that problem before missing something important going on that I should really focus on.
I'll admit I was not tied into the boat that day. Winds were pretty light and I didn't feel any concern. But, you guys are right, I should be tied in.