I'm a long time PocketSmith user currently switching to Quicken. PocketSmith is a decent product but has some glaring issues that don't seem to be on their radar and I feel like my finances have honestly become too complex for PocketSmith's simplistic philosophy.

Quicken is the 800 lb. gorilla of personal finance and has been for decades. It's fairly complex but also way more feature rich than most personal finance software. My main complaints about it are that it's a (mostly) Windows Desktop only platform and that handling attachments is more time consuming than PocketSmith. In reality, PocketSmith doesn't handle attachments that well. I just built an app to help streamline the process which is not an option with Quicken.

We run a couple small businesses along with our personal finances, which Quicken accommodates just fine.

What personal Accounting software are you using and what do you like about it?