You have a house with 72k ARV, 37k purchase price and 20k necessary repairs (do you have comps to justify 72k?

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

Is there enough demand from Oct thru April to justify a STVR?

It's hard for me to justify  unless that is the only entry point I can manage.

The other though I've had is, its small enough difference, I should go 5 and can always refi before the term if rates have dropped enough to justify.

It is mainly questions about the property or things to justify your experience and make sure that you aren't some average Joe just coming and taking a look at the house.

I'm trying to evaluate the purchase of a property for Airbnb and it's tough to justify dropping $99/month except for maybe one month. 

In many cases I think the financial upside with STRs can justify increased tenant-screening costs, and potentially even some revenue-sharing mechanisms with neighbors.In some areas, the government collects a tourism tax from guests, mitigating strain on local resources.

I consider myself pretty plain and I just don't see where the extra cost is justified.  

I can see this justified in several ways.