They did a decent job keeping up with PF1. They apparently got screwed with HLO when the dev who first worked on it put in a bad architecture, and the they had to replace that dev and spend quite a bit of time rewriting it. However, the biggest shame is the terrible support for homebrew. It’s a shell of what it once was.
Yeah, I was a big proponent of offline HL--did some a full .user file for a Savage Worlds setting and everything. But I'm not a fan of HLO, even if I understand the problem it was addressing for them. Probably obvious from my use of Maptool rather than one of the remote managed VTTs, I'm just not a fan of being dependent on anyone but my ISP for the ability to run a remote game.
We did use the campaign theater thing for a bit before we switched to Foundry. It took too many clicks to do things, but it worked really well. I actually liked it more than the PF2 experience in Foundry, but I didn’t want to have to maintain a HLO sub and ask my players to do likewise (to share materials).
Though the way they did that is fairly painless; even I can't bitch about $5 every four months.