I'm about 10 years behind you, but after a couple of decades gigging and at one time pushing 250-300 gigs a year(mostly country, blues, jazz, and theater gigs), there are a few things I've grown to appreciate.
Reliable gear is a big one. That means not only can I trust it to function, but that I can rely on it to sound good in whatever situation I find myself in. A mid forward sound is necessary in some situations like the dreaded banquet hall

I have also found that mid forward cabinets with less low end(ie// Schroeder, some of the Barefaced line, etc) tend to work well in most situations. Most of my work these days are IEM shows where there is no amp on stage. Or if there is one, its just to look the part. I like passive basses. I find they sit in the mix the way I want. Usually its a P bass or a 5 string Jazz. I always use a compressor. It slots the bass in the mix better. HPF's have been around for a while, but I think now that they've caught on there are some great builders making them. I think they're a must have. You don't necessarily need it all the time, but they are a lifesaver for some rooms. Lots of great experience in this thread! I've enjoyed reading it!