The fleas are back!! They never chew on me but it hurts to see Beau itching all the time. I took to reddit to try to figure out what was growing wrong with my treatment regimen. Some of the responses from my post were useful but most were sympathetic. I was warned away from flea collars as they only protect the neck area or can cause chemical burns and irritation.
Cats: Unlike my home town, San Jose has a lot of stray cats. I used to think they were cute until I realized that they are infesting my yard with fleas. Because it is hard to keep the cats away from my yard completely, I decided to take apart the past residents dog shelter so that they did not use it as a home during the nights.
Baths: It is not stated on the package of flea ointment but it is recommended that you wait a couple days between a bath and applying the medicine. Apparently the ointment sticks better to fur that has oil and baths generally strip the oil. 2-3 days is enough for the oil to return to the coat.
Medicine: I ended up asking my vet over at Whole Pet Vet and he said that flea medicine bought from vets offices come with a better guarantee/replacement process than those bought at pet stores. They recommended that in the future I purchase the same brand through them and they would deal with the company if it still failed me.