Congratulations on the milestone. Yes, longer is easier to put up.
I usually wear a topknot for sleeping.I have a 2-tine rather short hairfork that works well for this (tines pointing forwards, to avoid holes in the pillowcase). If my hair is damp I put it in a low pony which usually dries by morning.
I've never had problem 1, but I'd suggest just dampen the bent parts and go on with the day.
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