Hello,I have a property I sold and carried the note for the buyer using Owner Finance. 

Of course there are discounts for security measures, gates, guards etc. that everyone would get but homeowners premiums are derived on so may factors such as insured age, household members, claims history, ROOF AGE, age of the home, scheduled property, pets etc., so if each home is individually owned this would be near impossible. 

Assuming you are not the owner do you have an agreement to broker the properties with the owner?  

Not to mention the emotional toll it takes on a property owner and the aftermath of finally getting your property back then perform expensive repairs.

I collected a bunch of MTR comps on furnished finder, ran the numbers, and found that for one my typical 1 br/1ba places, I'd get maybe an extra 15%, but only if I allowed pets (all the MTR comps I saw had noticeably higher rents if they allowed pets...I don't know if that was just a fluke, but it seemed pretty consistent).  ...that extra 15% I found was after I deducted allowances for vacancy and the cost of furnishing the place (though, I'm not sure my vacancy estimates were accurate)... 

I like getting a HELOC on a property while I am an owner occupant, and keep it as an emergency fund.  

I want to take the proper steps to collect my funds and or put a lien on the property whereas I would receive my money if the owner sell a property.T.I.A.

I'd like to take legal action against the tenant to collect the amount I'm owed, but I don't think I can file a small claims case, since the water bill account is in the owners name (the account must stay in the owners name for legal reasons).

I highly recommend house hacking to get started, and as you mentioned taking advantage of low down owner occupant, first time homebuyer loans.I know the CT market very well so happy to connect with you if there’s any interest! 

So, that's what you could do...so if you want to go through the owner financing step through your family member just use those numbers as your baseline.