The short answer to your question is: Yes, you absolutely need an insurance product specifically catered to short-term rentals.

For a property to be eligible for 1031 treatment it must have been purchased with the intent of holding for productive use - not for resale.  

His philosophy is if wages are stagnant, then there won't be any raised rents and therefore, there won't be any merchant builders adding new product to the area.

If he knows what he's doing or has someone he trusts, then building and selling is probably the most productive way to make a gain out of the property. 

Is this flashing product good or is another material better?

One rule of thumb that I have learned from hanging around a very experienced lender is that portfolio loans are typically not the right product unless you are getting more than 10 properties.  

I have resolved that some sort of gutter-clog prevention product is the only option to prevent myself from having to get on the roof every day for 4 months.Do y'all have any recommendations for the best gutter product to solve the problem?

I took a cursory look at some of the product.  

They took a 5 acre parcel I had purchased to build new transmission lines and re-conductor old lines in order to provide power from a new utility scale solar generating plant (solar farm) they had constructed.My attorney hired the appraiser with only 2-3 weeks prior to the date our expert witness and discovery production had to be turned in to the courts.The appraiser found very low comps in the area.

Before you get on me about reversion cap rates know that we used some fairly low rent growth projections AND this same product type just traded in mid 6's.