Where do I start?
It was your first time.
For next time, leave as many halyards and lines (and sails) connected to the various spars as possible. Cuts down in rigging time and prevents "left-over" lines in the boat with the mast up

You'll get there! (It was your first time).
One thing I don't have difficulty with is tacking in light air. The DS is great, it's so heavy that once it gets moving, you can coast through a tack on momentum. However, there are some caveats:
1)
don't stall your foils.1a) rudder - don't oversteer. Yanking the rudder over too fast will stall it and drag it through the water like a barn door. Instead of spinning the boat on a dime, go for a well-defined curve. If you stall your rudder, straighten it out, let the flow re-establish itself and then try to steer again.
1b) centerboard - if you lose flow over the CB you will simply drift sideways. Always keep moving.
1c) Don't pinch! (Avoid the temptation to point higher than possible. All you will do is stall your foils and you will drift sideways)
2)
keep your sails drawing2a) don't let the jib go immediately. It will continue to draw on the old side well into the turn. Let it go when it wants to come over, and don't sheet it home until it has come over by itself.
2b) Backing your jib on the old side will help push the bow around (true) but at a cost of precious momentum. This should a tactic for other kinds of conditions (chop, etc.) where there's otherwise enough wind.
2c) Backing your jib on the new side, will prevent you from completing your turn and slow you down. 2 for 2.
2d) Don't sheet home your jib too aggressively, let the DS build up some speed a few degrees below your target upwind heading.
Almost every time I come to the dock from an afternoon's sailing, I have to tack upwind in narrow channel while the wind is dying (and blanketed). I really think the DS handles those conditions surprisingly well: I have been known to pass lighter dinghies on that stretch, mainly by coasting directly upwind for a boatlength or two before completing each tack. (The power of momentum).
You'll get there! (It was your first time).
Before I would be comfortable to attribute anything to your bent mast, I would like to have you tell us more about it. With the boat on the water, if you weigh the main halyard down with a shackle, where does it touch the deck in relation to the mast? It should be some distance behind the mast in a straight line. Is it over to one side? How much? Can you correct for any deviation by adjusting rig tension? If that's the solution, is the adjustment within reason?
Outhaul. There are two holes at the back of my boom casting. Original setting was to tie the OH to the sail, run it through one hole, run it back through the sail, through the other hole and forward to the cleat. That gave a nice purchase. Next, I tried lashing a double micro block each to casting and sail. That worked well, for the purchase, really smooth, but the blocks would touch before I hit maximum stretch on the foot. So now I use one block, but run the line through the grommet the sail. Bit more friction than two blocks, but enough room to stretch.
Mainsail. I ended up replacing the shackle at the top of the main with a knot. Gave me an extra inch.
I don't think I have a definite conclusion as to why your main wanted to be trimmed for off-wind, but perhaps you were sailing off-wind without realizing it. See the following:
Wind indicator. If you forget again, sail without one. It's good practice. Also, these things can be asymmetric if you don't take care aligning them. So you think you are sailing close hauled on both sides, but really you aren't. I always watch where the jib luffs, or where the tell-tales flutter (you have those, correct?) and, if necessary, re-calibrate where I expect the tail of the wind indicator to line up on each tack. I've found, though, that watching tell tales you can get tricked into sailing too deep, by 10-15 degrees. They work best if you are truly sailing close-hauled. I wonder whether that happened to you. I had to have someone point this out to me from another boat once, because I couldn't tell from inside the boat that day.
You'll get there! (It was your first time)