(When I bought my SFR, my insurance required to fix a crack on the steps before it gets insured, it cost me $500).2.

If you do have your own license - How much does that cost you to maintain each year, including insurances?

Are most Vendors who Supply & Install Licensed, Bonded, Insured in the same manner as GC's?

What type of property insurance can I count on?

I used to put all my houses in LLCs until I heard a podcast with an insurance executive. 

Is an umbrella insurance enough?

How do you normally handle insurance?

I also handled all the paperwork including tax, insurance, etc.The condo was in fair shape, but many of its components were dated.

Insurance companies require evidence of damages and expenses - it stands to reason AirBNB would also require such things.That said, they should be more specific about things such as why the invoices you did submit were not adequate.  

I have never painted brick but I would think the hardest part would be to get good coverage...you’d need a really fluffy roller to get the mortar joints.