Crack was repaired today. Good news is it did not go into the fiberglass and was just the gelcoat. Now I just need to figure out bottom paint to go over that area... pretty sure it is Micron 66 blue but hate to have to go spend $300 on a gallon of it, especially when I want to use something else on the next repaint.
Also found a trailer repair place here in Sarasota that had a large enough lift for the boat (Barry's Trailers in Sarasota, FL) and will be having the bunks redone to be closer to the original specifications.
Thank you to everyone for your help! Excited to have this saga come to an end.