How do other regular condos perform versus them? 

My wife and I spend a lot of time together, we take vacations regularly, and I prioritize my health by working out 3–4 days a week and getting 7–8 hours of sleep most nights.

Might be an additional cost there.If units are updated, capex items look good, leases and tenants look solid, and there are no other regular expenses besides the 5200 in insurance/property taxes then I like this deal.  

If seller financing is the route you go, you might consider getting creative with the structure to make it work for both parties.

@Timothy Frazier I wouldn't use the word bad because if that is the route needed to acquire a piece of property then mission accomplished however you are stacking the deck against yourself with this approach.  

Is becoming a real estate agent the right route?

I have studied things and I feel I would only make maybe an extra grand a year and frankly I don't want to squeeze every last time out of people coming for vacation.Most of our guests are regular people.

An easier route would be to convince him to go in on the short term rental together in a partnership. 

I am seeing a crackdown on STRs not so much as a result of any hotel lobby, but as a result of regular citizens complaining to their elected officials that they don't like living next to a hotel.Can't really blame them.

I am self employed but have 6 employees so i went the SEP IRA route to defer some of the income tax.