Welp. Not able to get the dipstick tube out yet, but the good news is that in my quest to squish it inward enough to grab it, it closed off the hole. No more oil leak.
Also adjusted my timing and figured out why it was cutting out. Set the timing at 18*. The fuel issue was actually my inline filter clogging up. Had some weird white milky substance in it. Pulled the filter, shook some gas around it, and drained it out. No issues after that.