My answers are; if you don't believe you can do something then you can't and if you don't have a good business model in writing, or in your head then you are only 'WInging It' and any success will be totally reliant on being lucky. 

You'll have way to many questions when you begin, so I encourage you to write them all down and ask different individuals to get an answer.

What is the best way to fund this super-expensive repair without just writing a check and then, crossing fingers that the insurance company will pay up? 

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

I am writing because I was impressed with what you replied to Wendy, and am looking to connect with other Investors. 

Can I ask her to put something in writing?

My thought is wait until we move out to next home, then redo the bath and kitchen with the new carpet and paint for the renter... then its  a write off... yes not able to enjoy it, but it wont be fancy by any means. 

I contacted the district attorney's office, in writing, and was able to get a solution shortly afterwards.

As of this writing, the license itself is called a Transient Occupancy Tax Certificate (TOT).

Some carriers are known for getting in certain markets, holding those accounts for a certain period of time, and then pulling back from writing anything in that industry for the next few years.