You won't regret it, @user3509!
I jumped over from ST a few months ago and zero regrets. Everything on HE and webcore working perfectly and more quickly, after correcting small issue with HE/ST versions handling date/time for timezones differently, and twc weather not supported on HE. Started converting several of my pistons to HE's rule machine, but have not noticed any difference in performance. All way better than ST's laggy web interface.
No need to wait til Jan...just do it! Just took me a couple hours to move 90% of my physical devices over, the rest of the day to deal with a few z-wave pairing issues (f-ing i-Blinds!), and the rest of the weekend to recreate virtual devices and webore/rules automatons I had before. My setup has around 80 physical plus virtual devices and around 30 automations, and integrations with Rachio, Flume, EcoBee, Actiontiles and data logging to google sheets. I was afraid converting all this would result in more bugs that were going to take longer to fix, but with this community's help, most of it up and running after a weekend, and just a few weeks to tie up some loose ends and move on to building the system out further (including Emporia Energy monitor, and some new rules using Emporia and Flume triggers/conditions that weren't possible on ST). I think all the best Groovy developers that helped make ST what it was, are on HE now. Some key pieces here from my ST setup were @sandood's ecobee suite and @krlaframboise simple event logger, but many more cool things I've found in built-in and community drivers I'm using now (+1 for HPM package manager, if it's not built in, chances are you can find what you need there - only a few items I've had to copy/paste code or Github URLs.).
As @Equis mentions, only painful part for webcore is going through each piston and selecting all the new devices on HE hub. When you restore backup pistons from ST version, all the devices show up with a unique, but not user-friendly code, My only tip to my former self would be to print each of my more complicated pistons with the ST device names I recognize to ease this step. I didn't make any mistakes, but there were a few cases I really had to work through the logic again to make sure I was picking the right physical and virtual devices.
I am not an "everything needs to be local" guy, and zero issue with editing on the web, but love the faster local piston execution on HE. It is definitely noticeable. IMHO if you want to host webcore on Pi, it can wait if you are happy with how it worked on ST.
Welcome to HE community, and hope your conversion goes as smoothly as mine.