No flags went up and I will be looking forward to viewing more of his properties.

Never pay any upfront fees...always a red flag.

Whether they paid by carrier pigeon, a drone, or however they chose to send it and deliver it to me, was on them.  

All the red flags are present that are needed to convince you to run from this "deal architect" (ie scam artist)

And if you are loosing money every month that is red flag.  

You may also want to talk to the current carrier.

As of August 19th, we are half way through payment for August but, that was never the agreement (to pay our monthly rent the 1st of the month) Those two situations were an extreme red flag and, now we feel bummed out because we now see that this young man was never trustworthy to start with.

Then the person you validate with comes back and flags he whole thing.

Even with $40k in repairs, you only have to rent each one for a whopping $125 per month to match the 1% rule....Which raises major flags for me.What kind of condition is the building / units in?

Above is a very broad example of how insurance carrier do it.