Definitely do a proper shampoo and conditioner first (I don't have beard special stuff, love the superdrug own brand conditioner).
My wife doesn't expect me to cut it off, no problems with that, and generally I can get by calls for the barber. I don't bother with getting it to look good, the bands are just to stop it getting individual hairs getting pulled.
Some hairs are wirey, some are dry and split, some seem to be two hairs stuck together that later split. So seem to be completely monstrous, growing only a short length, but feel more like a cats whisker at the thickest point. Weird and wonderful word of beard hair. Recently I've been finding one or two that seem to have growth rings on. Small bumps, like extra thick, but very evenly spaced a few millimeters apart, I'm thinking it's something to do with daily growth?
As for the moustache, on the occassions I did shave it off, or the barber trimmed my moustache, I just power through the annoying phase of it irritating my lips, once they get a bit longer, it's not longer straight on the top lip, but rather going over, and I don't really notice it any more.