Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

network, learn the area and execute. can be tough entry as a lot of people are ttrying to get into it. 

I disagree with you regarding materials, however.

Not sure about FL, but many places don't publicly list the purchase amounts, so tough to know what they sold for. 

-Multi-family here is a little tough to come by.

Sorry, Boulder won't work; it is a tough market.

In terms of the upcoming zoom meetings- asking tough questions is difficult.

You should split the costs - labor and materials together.

The liability coverage is way better, the building coverage is often better, and commercial policies typically cover loss of business income as well, which a homeowners policy isn't going to help you with.California + wildfire area + STR is super tough. 

@Justin Sherman, this market is tough to make the numbers work because of what you mentioned - high rates and prices still rising.