Those are all good questions. A phrase that's stuck with me and worked well is "it's never bad to take profits".

Whatever your initial investment was might determine the maximum amount you might want to take off of the table. 10% seems to me a reasonable amount to profit.

I'd be sure to sell crypto that i've been holding for over a year to insure you wouldn't be paying short term capital gains. Any coin that you have not been trading and have been holding would seem to be the best choice to keep your taxes simpler.

If you don't flaunt it I don't think anybody will treat you any differently. I think it ends up being more to making an adjustment to the way you feel about yourself because as you say "I am living in a more comfortable place".