Wow, I read this thread when there were just a few posts and it looked like Scott was getting the help he had asked for. I didn't bother coming back until I saw an apology thread and thought I must catch up.
Obviously there are a lot of different opinions out there. Trim definitely effects performance, but it can be at a cost. I don't mess with my outhaul much, I am usually pleased with the way we are sailing the way it is currently adjusted. Perhaps I'll look at it more this weekend, perhaps not.
We sailed a lot in the past with some great cruising buddies and we would basically "set and forget", meaning we would set our course, engage our tiller pilot adjust the sheets etc until happy and let her roll. That was on a 25.5 and I would mainly adjust my sheets while sailing to account for the gusts, lulls, and shifts in the wind. I almost never touched the outhaul. Our friends (the husband) would constantly tinker with the sail trim and spend so much time trying to get it right that they would usually end up falling a little off course or something frustrating would happen... we'd watch them while sitting back lounging and they looked stressed out. Not what I am looking for when I am out there, for me it's about decompression from all the stress I already have in my life, I am not looking to add more.
Hermit, I'm not sure if you haven't, but if you haven't raised your sails (even just one) and cut the motor off to be under sail power, you haven't yet experienced the magical feeling of being powered by the wind alone with the quiet (since your diesel is off). There is nothing like it and every time we cut the diesel off, my wife and I smile at each other and have that feeling of "oh yeah, that's what it's all about!".
My advice for you, which you may do what you want with, is just to do your best to get the main on as best you can, but don't worry if the trim isn't 100% perfect. Go out on a light/medium day (if you get those). Point into the wind, raise the main, fall off the wind, kill the diesel and just enjoy the first couple of times out like that.
We've sailed our mast head rig plenty of times under main alone and ours doesn't have big problems sailing to wind... your boat is probably similar enough to ours that you may find the same thing. If you do have issues getting where you want, you can fall back on your diesel to get back upwind if you need to, at least you will have past that milestone on that boat that you have worked so hard to restore. Worry about trimming and tricking out the sails perfectly later.
For us, yes sailing is more like a religion, one that brings us close together and closer together with the great beauty of this place that many people don't get to enjoy the way sailors do.
Don't get me wrong, when there is another sailboat around and I'm in the mood, I might tinker a little here or there to make sure I'm a little better trimmed... I'm sure 'Pocahontas' would let this forum know I'm always in the mood for a little impromptu racing when another boat is around, if I didn't mention it...