I just traded in my 2014 scion FRS which I was upside down on.
Background: A mutual friend had put me in touch with Chris, the head of the internet sales department. Chris was very upfront about my situation and what was needed to get me out of it. However, the first two times I just couldn't believe how bad of a situation I was in with my scion, but called in every six months to see if my situation improved.
The Experience: However, this last time I was a bit shy to call in again given I didn't want to waste his time calling in and not executing on a purchase. I ended up getting the appraisal done online (which is a bit lower than when you sit to negotiate) and their sale person, Jacob, reached out to me to see how he could help me. I spent a good day going back and forth with him on different cars and eventually locked down a list of 3 to compare. I headed in on the second day with the list. Test drove all 3 and then sat down and looked at the numbers. He was very open and upfront about what we were dealing with and was very patient with 0 pressure. This was the complete opposite experience to the other dealership where I had bought my scion from. Jacob restored my faith in the car buying experience and I even got a chance to meet chris, an equally stellar guy!
I would encourage everyone to give the online experience a chance and work with them. Tell them what you need and what you are looking for. If they can do it they will let you know. They will work with you! Net scenario I walked away from a car that was no longer fitting my lifestyle. Further, I don't believe I added any additional negative equity to the burden I was already dealing with over the last few years which is setting me up for future success. Also, when comparing the purchase price of the used car to the suggested price of a certified pre-owned car on KBB it was within a few hundred dollars.