Technology

I've not hit any pricing gotchas. They've made it really clear when you're about to go somewhere that costs money (with clear "upgrade to pro" or "purchase" buttons if your account doesn't have access to a feature) in my experience. Personally I run the free tier on all my domains (although I'm getting to the point where I'm thinking about the 20$ personal tier) and professionally I run a few sites on the 200$ business tier. In all cases and for all domains I've not seen anything that red-flagged for me as a problem. I think I'm quite sensitive to that sort of stuff personally. I've dropped vendors for pretty petty stuff professionally. Actually in the professional environment I have a case of a managed SIEM arguing about Cloudflare being at fault for an integration problem. Cloudflare's documentation has been stable and actually leads me to believe cloudflare over the SIEM.

Lost data would instantly make me look for alternatives. I don't know much about dodgy management... but official support has been stellar and account managers have been very helpful while not pushing me into products that are not a good fit (literally had one of their engineers outright say, this isn't the right product for you based on what you've told us while on a sales call).

Your experience may vary... I could just be really lucky and happen to get the "right people".