The hardest part of my one SMS run was where I spent like 20 - 25 mins in Pianta Village trying to do Yoshi Skip for Village Underside during the run without either practicing beforehand or planning from the beginning to use a route without early Pianta Village in it like a sane person. Eventually I gave up on said oh well to my splits and went to Gelato or whatever it was instead.
That's cool that you're using your own route. Are you active in the Prime speedrunning community?
'Official' Plusle of the SSBU board. Also, creator of that thing down in the line under this. http://www.gamefaqs.com/boards/997828-paper-mario/57781633