I'm not sure that I could be described as 'wise', however, I'll weigh-in with my experience.
I experienced the same issues as you both, but was sleeved in New Zealand in September 2015. I had a number of months with a normal recovery, then started to experience the same as you both - difficulty tolerating food that I could previously tolerate (but this was erratic), and also worsening restriction over time. Several dilatations did not help and I needed a stent. The stent helped enormously and although it was awful when it was in it was like a miracle when it came out!
Although I still have trouble at times almost a year out I've realised that it's about how well I chew. I can now eat anything I like (last night sirloin steak) but need to chew the food very well. Obviously very small amounts. Even minced beef or cooked onion is not good if I don't chew it well enough - I read somewhere food needs to be the consistency of apple sauce when swallowed ie, soft, pulped and wet!
If I have trouble I tend to have a couple of days of trouble and wonder if it is because the stomach is irritated or swollen. My symptoms are as you describe SharBear, tightness and gloopy saliva until I get rid of the food that is causing the problem.
My advice (for what it's worth, and I'm sure you are doing this already) is to see your dietitian or Dr and to record what is giving you trouble, and to pay attention to what (and how) you are eating. Keep fluids up. I don't think you should be experiencing pain.
What ever you do, don't let it go on and on, I found the problem to be very draining and impacted on my day to day life significantly. I also lost weight very, very fast (far too fast to be healthy) and was very weak and unable to work.
Good luck and keep us up to date!