I have had wonderful renters each year, relocations to my area who need temporary housing, but this year have not had even a single inquiry (priced the same as previous years).

Even without those challenges you had, it was still probably hard to find a buyer because of the use mix.  

I always tell clients to take care of the hard job first - If this is a sellers market then find your property and even get it under contract before you sell your old property.  

It all evens out.

I filled out their survey and provided some constructive feedback, even though I don't own a STR here.

Quote from @Paige Seeley: @Jay Hurst even with 20% down, what non conventional options are you talking about? 

Dennis' dad and I actually tripped over something similar back in Chandler.. we learned to tap into city planning websites and even call the permit offices directly to get a real sense of their backlogs.

I’d love to hear your thoughts, tips, or even warnings.

@John Lasher If you are still looking to spend $20k-$30K for a coach, I would be happy to take you up on that offer :) For full disclosure,  I will share with you precisely what you can learn online/ perhaps even entirely through these BiggerPockets Forums but that doesn't address the reason why most are still unable to purchase larger assets: creditworthiness and capital relationships.

Long-Term Rental Rules: Even though my properties are long-term rentals, are there any tax benefits I might be missing if I occasionally rent them short-term?