You seem to have the classic sub 2nd met pain (“metatarsalgia”) with your foot mechanics (i.e. slight bunion drift causing the 2nd toe to “hammer” and retrograde pressure down on the met head - you seem to have a good grasp/understanding of this). Good that a plantar plate tear/injury has been ruled out - often missed, even by good practitioners.
You have been addressing your mechanics correctly so far (1st met cutout/“reverse” Morton’s extension, met pad, etc.), but this won’t work forever (even in my “normal” pts, let alone someone running the Leadville 100!).
Yes, hammertoe surgery should be curative - for a while. Depends on what surg and you should carefully discuss this with him. A simple tendon flexor tenotomy won’t have much down time, but is definitely limited in its effectiveness. Hammertoe surgery will help longer (with or without fusion the PIPJ), but this may still progress if you don’t deal with your hallux valgus deformity as well as this always progresses in time. But, that “time” could be 20 years from now, and you really don’t want to address that unless you have too.
Good luck!