If I paid cash for this property, the HOA + Insurance + taxes is around $500 / month. 

If you want to get a clue about places to avoid investing look at states where insurance premiums have jumped or where homes are uninsurable. 

He ensured that the structure, HVAC, plumbing, and electricity were well-maintained, and rarely had anyone coming in for maintenance fixes.

.$275000 with 25% down, taxes $4080, insurance is 3000 yr and rents is $3800 month, Water $400 mth. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

I also assume you have homeowners insurance rather than landlord policy which is invalid if you’re not living there.

The cost associated with insurance for not having 20% is peanuts compared to what you potentially can do leveraging your down payment. 

The purpose of the post was to find another resource for property insurance (i.e., agent).

Instead of evicting them, i was thinking is there some way that I could rent it back to him for very cheap (mainly to cover just the taxes/ insurance) ie 2k a year rather than the going rate of 2k a month for similar properties.

It’s cash flowing about $50/month after everything (PITI, flood insurance, home warranty, excess liability & termite protection) - if I got ride of termite it would cash flow $125.