Seems pretty simple: only justified reason to finance money is to earn a higher return on that borrowed money.

If you have increased the value enough to justify a refi, refi it before renting the 2nd unit out so you can get owner occupied terms.  

Since we will be visiting a LOT, we thought it might make sense to by STR near there....but I really don't know what tourist attractions are in/near Dallas that would create a reasonable occupancy rate to justify the cost...

In my opinion, my education and experience would justify to the IRS that I am perfectly qualified to do cost segregation studies.

They need to file a claim with their insurance provider, though I doubt the "damage" would be significant enough to justify the cost of paying the deductible.Your homeowner insurance does not typically protect vehicles because those should be covered by vehicle insurance.

There is a risk major unforeseen repair, do you think you this cashflow justifies this risk.

Did they reference a particular non-government backed loan type to justify this topic? 

I see it all the time, whenever I give customers a tour, which I don't do very often as I don't monetize them, so it is hard to justify spending a lot of time that way. 

So please take that into consideration when trying to justify the price.

Fees should be clearly stated, easy to understand, and justifiable.