We asked the owner if we could start painting the house before the closing date...

If so, you'll want liability coverage, which can only be provided by the owner's insurance policy.You want to be INSURED not just have in Interest (which only alerts you about policy changes).

The previous owner had it listed with them for weekly summer rentals.

After years and years of being frustrated by how tough it is to find honest, communicative contractors, I decided to start a Handyman/contracting business.This is NOT a solicitation.My question is – What are Property Managers / STR Owners / Investors looking for when they need a handyman and how are they finding them?

My brother lives above.3.  2007 house just updated by owner.4.  

They said it didn’t matter what Lee Arnold, the owner of the company, told me, the money wasn’t available yet.

With all respect to AirDNA and the amazing data they provide for STR owners, their pricing tool is not on par with most tools available there. 

The only way I could see it happening is if you deal directly with the owner and they are willing to accept Bitcoin. 

LLC's are still the way to go but yes you can't tap into owner occupied mortgage tools such as HELOC's or high leverage.

And there are even more carriers who would insure co-living rental w/o owner-occupied - for example Obie.