Yep. I think you hit the nail on the head.
Funny too, because before he started dating Jenn, he was following a fairly decent path.
He was a well-regarded player on Lake Mary H.S.'s water polo team. Graduated in 2000.
He stated before that he was in college when 9/11 happened (2001); he had also said in a recent Discovery Cove vlog his ultimate goal was to become a marine biologist or something dealing with marine biology / marine life. (not sure when he dropped out - if it was before or after Jenn)
He was placed into a temporary coach / instructor role - likely related to swimming / water polo - in Seminole County Schools (2002 - 2003).
I'd imagine he was also working for the Orlando Science Center and / or helping Jaime with his construction company during that time - or shortly thereafter. To his credit, he never seemed to be a job hopper regaling the viewers with tales of 5,487 different jobs like Jenn has.
He started dating Jenn circa 2004.
(for reference, he started YouTube in the summer of 2009)