I know I’ve heard this can be a red flag, but I’m wondering why it would be a problem?

You have to keep in mind that 1 in 8 Americans lives in California.

Does refinancing send any flags to a bank that would cause them to deny a traditional loan shorty after the refinance?

It is hard to get a company based in the US to finance a purchase in another country.If you use local lenders of that country the interest rates are going to be a lot higher than what you see in the US.Downpayment is going to be above 15% and there are taxes involved in the purchase in the south american countries I have looked at. 

One red flag to me was that he didn't really want to pull permits for the work.

Instead of canceling rent and sending hundreds of billions of to big corporations, they could provide a small subsidy to all Americans for a few months so that they can pay their rent while this is going on. 

The biggest red flags I see!

Review your monthly statements and if any red flags come up, notify immediately.  

I’ve been with American family for over 20yrs...and can’t complain, but seem like it is time to shop around as the premiums are getting a bit crazy.

I launched my business this year at the beginning of 2020 called American Freedom Homes and went ALL IN.