I feel like your clues are tricking me, haha (or, more likely, I’m just really overthinking this all). I can’t think of what issue would be worse on soft footing yet completely fine in two months. I’m seeing a left hind lameness that looks like it’s during both weight bearing and swing. I’m guessing stifle, but I have no guesses on the what.
I’m also seeing LF but that could easily just be referred from the hind, rather than anything there actually bothering him. Since you mention chronic issues I’m getting the feeling there my be something spinal (very specific, I know, haha) but I don’t think it’s fair to judge that with him so ouchie elsewhere.
He’s a cutie…glad you got him patched up…I can’t wait to find out how!