Also, every now and then I think about the guy that lost 28000 Dash on a bet a few years back. I don't know how he deals with that when he sees the price now.
And how he will deal with that when he sees future prices.

What was that bet?
He was martingaling and hit a run that wiped him out, he's fine though, learnt the lesson, moved on with his life, bought a house last year and even swallowed his pride and got back in to DASH early last year, he's being successful and earns well in rl so built up a nice stake of masternodes again.