Welcome to the community, Timothy! 

DM me, and I’ll point you in the right direction!

But then comes the bombshell..."

I will say that even though you get the boost from VRBO and AirBNB, the first year of operation is usually lean as you build up the rep.Offering a discount on the stay is a way to be more attractive but don't go crazy.

I'd get a quote from Steadily as mentioned, but Thimble is another one I read about in an AirDNA article.

Now were back to a mare normal world where a person has to have that skill of forecasting, analysis, ability to "read the tea leaves" for where it's all going and if todays acquisition makes sense. 

I have been referring the people to the prequalification form that RentRedi uses prior to setting up a viewing.

No apologies needed for the tough love.   

I ended up pulling the window, installed a plastic window sill pan and adhesive flashing plus I added a L flashing on the exterior of the trim along with fully re-caulking the whole thing.That fixed it and it has been dry for the last 4 years or so and we get a lot of rain here in WA.

I have read in forums that upfront fees are generally big no-no's.