for the most part I’ve always been the guy that is thinking “I wish I bought in way back when…”, and I’m resolved not to be in that position again

Sounds like story of my life lol. Didn't get into crypto in 2014 cause "it was dead", never will I make the same mistake again. It's life-changing wealth or bust for me.

As for putting more fiat into crypto, I think it's a decent moment to do that, personally I'm still saving up for a couple of months, as I see the market tumbling down one more time before the bear sang its final tune.
And if I'm wrong, I'll still be buying Bitcoin at a decent $10-12k, which down the road will look like peanuts.