New Bilge pump
The bilge pump failed during the delivery trip to San Francisco bay. It turned out to "only" be the float switch, but given how relatively inexpensive bilge pumps are I opted to replace everything. New pump, new switch, and new wiring. The old wiring was heavily corroded, and if I like to only fix things once. I knew if I didn't replace it that it would be problematic.
Replacing everything, however, was not enough. The new rule float swtich failed during the first big rainstorm. Luckily I decided to check on the boat right after and found the bilge filled with water. I was able to manully run the pump without any issues. I have since replaced the Rule float switch with a Johnson. I will be checking it often, and connecting a counter so I know how many times it cycles.