I travel there more than I should and never thought about the short-term rental market until now.My biggest concern is always the permitting/compliance when entering a new state/city but they have an entire page dedicated to it so that makes life easy.That being said is there anything that a "non-local" should know about besides the regulations?

@Michael Marquis Angie is right that using some technology and basic CRM automation off your own website is a good supplement to what you're doing as far as personal networking. 

This property consists of main cabin (permits in place) and a tiny home which is built without city permits.

One thing I would suggest is setting up a automated transfer payment for at least the amount of your minimum monthly payment.  

No pets (with the exception of medically necessary pets) of any kind are permitted without specific written permission of landlord in the lease document, an addendum to lease, a non-refundable pet fee acceptable to landlord and/or an additional pet deposit or additional security deposit.

Don't forget to pay the $10 sales tax permit fee.

Ideally, you want several employers to spread the risk associated with a dominant industrySupply and DemandCensus.gov under the “Selected Housing Characteristics” tableDetermine by analyzing the five-year rental vacancy rates and median rental rates in the market, as well as the year-on-year change in the number of building permits created for commercial properties (five or more units)The number of five or more unit building permits won’t tell us much on it’s own.However, a huge red flag to you would be when you see an increase in the number of permits in combination with an increasing vacancy rate and/or a decrease in median rentsAs vacancy increases, median rent and new building permits should decrease… and vice versaBest Case:Low or decreasing vacancy rates and increasing median rentsDecent Case:High vacancy rate that is decreasing Stagnant vacancy rateWorst Case:Increasing vacancy rate and/or decreasing median rent An increase in the number of building permits (5+ units) in combination with an increasing vacancy rate and/or a decrease in median rentsMiscellaneousResearch Other Characteristics relevant to the strength or weakness of a marketExamples:Landlord vs. tenant-friendly state?

How do you automate your lot/garage/stall?

Those tasks are a lot harder to automate that looking up the price of an airline fare.

You need to live within 50 miles of a unoccupied STR, you need to be living there, lottery system for new permits and you don't get one, STRs are banned overall in certain zones, HOA votes to disallow STRs.