As to getting out of your slip, I think the main problem was handling, or mis-handling, the tiller on the engine, which should be very effective. With that, you can counteract any prop-walk, which should not bother you in a boat where the prop is not fixed. Small boats with outboards are much more maneuverable than inboards.
Jeff said,
Single-handed with non-tailing winches, do what he says but on the tack you probably won't get the jib sheet tight enough. Stabilize yourself on the new tack and then pinch up for a second with the sheet in your hand. When the jib luffs, haul it in. Like a man. You don't need no stinking winch handle.Beating upwind in a narrow channel is the toughest challenge sheeting/winching-wise, that's when you really need 3-4 hands. I've found that(yes, I know you know how to sail, probably a lot more competently than me, but I'm the one typing, I have the conch!) if you can get the new working sheet all the way in and wrapped before the jib fills on the new tack, it's pretty effortless: you don't need to tail because you don't need to winch, it's already all the way in. Admittedly this means you really need to keep some way-on throughout the turn to ensure that sheeting tight on the new tack will actually be effective: if you lose too much speed then you're going to need to reach a little deeper initially, which then means winching, which then means tailing, which then means you need 3-4 hands again. Of course, 50% of the time the jib sheet will hang on some damned thing mid-tack; the open bow hatch, a stanchion, the chute pole, a paddleboard, or a spouse/sibling/niece/nephew/pet, and the whole thing goes to !@#$ in a hurry and threatens to upend your gin/tonic, but that's why I sail around in circles in Henderson Harbor and am not rounding the horn. Got to know your limits!
As to those cam cleats for the jib sheets: Lose them. A hazard if you fall into them. The reason this was probably done was that if you mount the cam cleat on the coaming, it will be hard to lower the sheet enough to get it between the jaws. Two better ways to address this are: mount a block aft of the winch that holds the cam cleat at a proper angle, or use a horn cleat as Jeff suggests. You don't have to do a proper cleat hitch on every tack; just two wraps will do it and in fact, I would recommend never putting a cleat hitch on a sheet.
As to the storm jib or trysail: What the hell, man? Two deep reefs for the main and get yourself a headsail with a furler. Headsails meant to be reefed have a foam luff which will make for a better shape when they are wound up a bit. If you have the money, get a 100% and about a 135%, both with foam luffs. Do you really want to go forward when the wind is "freshening," as the old-timers euphemistically say? No.
Speaking of going forward, I suggest running the reefing lines aft for the main. I didn't do this in my big boat for several reasons, although a lot of sailors prefer lines run aft especially on blue water boats. I don't want to go into it, but I prefer not to. However, on a small boat that you will be single-handing, you're going to have a hell of a time going forward to reef if you have no self-steering. Even with lines run aft it is a bit of a circus getting it done in a blow, but hey, you could stay home and watch Netflix.