I even reached out to hosts on Airbnb, and one said to call the city planner to get my STR permit. 

I would call them first, let them know you are sending it and then send it via email and regular mail. 

Not all things you consider an expense are honored by the court.For example, in a Colorado Court of Appeals case, “the trial court found that the principal portion of the mortgage payments did not qualify as ordinary and necessary expenses for purposes of calculating child support.”It’s All In The NumbersAccording to the Census Bureau, “Parents who received regular child support payments received a monthly average of $604 and a monthly median of $396 in 2017.”

These are heavy-hitter, regular buyers.

Great tools that get updated regularly. 

. ** I’d ask for their Airbnb or VRBO profile link to review their reviews, years hosting, etc. to ensure it lines up with what they’re telling you*2.) with you guys being out of town, I’d make positive they have a team of maintenance guys for whenever something along the lines pop up.

Hey @Austin Wolff - You bring up some good points about knowing the house better than anyone when you build new if you are actively involved and onsite regularly, but I'd get behind @Jay Hinrichs, in the sense that the numbers don't always allow you to build new.Here in Chicago, new developments are super pricey, and even the BEST DEVELOPERS HAVE SLIM MARGINS. 

STR/MTR host here. 1.

You should ask a host of questions about how they handle situations and the systems in place - rent collections, maintenance, evictions, vacancies, etc.

I host one every few months.