I hear you @tracstarr . I was in the same boat when I moved to OH2.
If you are using or planning on using a raspberry pi with openhab 2 I HIGHLY recommend using OpenHABIAN:
The author @ThomDietrich has applied so many fixes (linux security, linux USB configuration (ie. OpenHAB user added to dialout), SMB shares for remote configuration/file sharing/Designer, on and on) to the RPI install/config “gotchas” that it give you back 90% of your weekends.
I was considering throwing in the OpenHAB towel until I found OpenHABian