(actually exterior first, also lawn, landscaping) You can pay for the materials using money from your HELOC.

Could an inspector look at the house at that point and certify that there are no asbestos materials inside?

The only quick number there might be is doubling the cost of materials to add in labor, but that's not guaranteed - some jobs have few materials and a lot of labor and others are opposite. 

If you were to partner with another more experienced investor to purchase a short term rental, do a cost segregation, and "materially participate" then you could gain the benefits you are looking for without negatively cash flowing, and you could work out a deal where you maybe only have to materially participate for the first year to claim your tax benefits and then you can act as a more passive investor.

"Most" water damage claims can be fixed and closed within a few weeks or months, where a fire claim "may" take 6 months to 1 year to close out due to more extensive construction, delays in materials or labor, weather/seasonal delays, etc. 

Let’s connect and potentially be future partners.So much material to cover.

You may want to read materials about "networking for a job":)

It's a nice-to-have in my eyes.I think what's more important is ensuring that there are proper incentives that reward those who are materially participating in the deal.

I just wanting to make sure he's not purposely overestimating material and then keeping it to use on other jobs.

I will spec materials/colors/repair method when I feel it needs to be done a certain way or I want something different/special.