there was a recent very thorough video done before I left the states in October showing the daytime bus ride over, the stops, the border process, and arrival into Siem Reap. It looked pretty painless.  I really don't mind the bus ride, I've done worse on megabus Pittsburgh to New York City on an overnight.
this return from Cambodia will only be my second time in Thailand ever. Have had no other legal or Visa issues since I have been here, and I don't plan on returning to Thailand until maybe the late fall/winter
definitely do not plan on living here. My goal right now is just slow-travel through Thailand, Cambodia, Vietnam, Kuala Lumpur, and maybe Singapore and Manila. This over the period of a year, and then just keep repeating this for several years until my passport expires in 6-
I'm actually sort of contemplating that now, just to avoid the hassle. But I actually booked the bus ride from Bangkok to Siem Reap, it's not that horrible (watched a very detailed YouTube video of a recent transit), and was only $47. The plane ticket on Air Asia is $151. This for the day after Christmas.