Contractor needs to know and understand the house hackers mentality and rehab loans.

I have done the cash out refi/HELOC simultaneously as part of my first deal and it was exhausting!

Commercial Umbrella (in commercial there is also "excess liability")An Umbrella policy provides additional Liability coverage if the underlying policies:   a) Home, Auto, Boat, rental dwelling, etc on a  Personal Umbrella   b) General Liability, Business Auto, Workers comp, etc for a Commercial Umbrellaare exhausted in a claim. 

Looking back I had the mentality that I have to sell them to free up cash and keep moving but clearly I dropped the ball over the past 10 years.

I get the whole by the book mentality, but I'd rather not piss them off over a day late when they always pay and it's not like I have to chase them down.  

., creative strategy to scale and form a cool niche.I’ve worked on several STRs at once, and found the approach exhausting.

Tim,An umbrella policy is a policy that provides additional coverage if the limits of the underlying policy (home, auto, rental dwelling fire, boat, etc.) are exhausted by a claim. 

Tenant further agrees that Landlord may continue charging rent until a replacement Tenant takes over or the security deposit is exhausted, whichever occurs first."

DSCR should only be used once you've exhausted your conventional and local bank sources.  10% and 2 points sounds more like hard money than a long term DSCR loan.

While it would feel good to shove it to them, evict them and give them the mental middle finger for causing you additional stress, and costing you an additional $360... it feels a heck of a lot better IMO to have a good tenant and keep a long relationship, and consistent rent.