I'm in this same boat. I've been looking at Hubitat for nearly a year now.
My concerns were/are: It's a pretty new company, where are they going to be in 10 years, or will it become a pay as you go service. (I guess ST would be in the same boat).
I also have a bunch of stuff that I'm not sure will migrate over. Granted I have not done a TON of research lately..
*Influxdb logging - I have a pretty extensive HA dashboard setup in Influx/Grafana
*Webcore - I rely fairly heavily on Webcore for lighting automatons.
*3rd Part smart apps - Such as BlueIris fusion. Using motion triggers from cameras to automate lighting.
*How does the android app work? Last I recall seeing it was quite cumbersome. (Wife friendly, etc)
You see that's the whole point of "local" - it doesn't matter where the company is/what they are doing in ten years. A "stable" configuration should last for the lifetime of your hardware - I think of it like an "appliance" similar to a refrigerator or stove. This is one of the compelling things about HE that got me to switch from Smart Things many moons ago. It's also been a great selling point to my residential clients.
I guess it depends on what you want to accomplish though..
Iāll let others weigh in on some of the other items, but if you know webCore you should be able to backup/restore over to HE and have your pistons back up and running with only minor modification - good news here is that unlike ST, webCore runs local on HE.
Hate to be "that guy" but search the forums - there are a ton of things available just takes some digging.
Yeah it's not the most friendly BUT what are you planning on using it for? Dashboard Access - HE allows for this so you don't need the app just a bookmarked link. Also there are some cool 3rd party solutions for example:
Also you might want to think about implementing a VPN if that's your thing. WireGuard is awesome and can be installed locally.