I normally research:-Location-Crime-Median House Hold Income (HHI)-Zillow - other similar units + B/B that have sold in the area (ex. 1-2 miles in the past 90-days)When contacting, anything you would ask aside from the following?

Whether it is loud music at night, or "Hey, our car broke down and we won't have all the money this month to pay the rent" - how you handle those situations.  

We got several quotes for cleaning and repairs, which added up to almost $4000 beyond normal wear and tear.

We love having a smart lock on the property, guidebook/recommendations are a favorite, and do move in/move out inspections just like normal!

Oh YES, I recall one where the low life tenant knocked the garage down with his car, YES took it down because he was being evicted LOL. 

Both own multiple LTR houses.Be aware that if you buy a STR in your SDIRA you can never stay in it or work on it while your IRA owns it. you cant stay in it even if you pay normal rates?

Ask your personal insurance agent (the agent you use for your property insurance and for your personal home, car, etc...) what they recommend for liability coverage in your rentals. 

You shouldn't be recommending people use the CAR lease if you're licensed realtor in Chicago.

.• 5-Bag Limit: Each resident is limited to disposing of five (5) normal-sized garbage bags per day.• Bulk Waste Limit: Residential bulk waste, construction/demolition, and green waste disposal are limited to a 5' x 8' truck bed load or small trailer per day.𝐂𝐞𝐧𝐭𝐞𝐫 𝐕𝐢𝐞𝐰 𝐑𝐨𝐚𝐝 𝐌𝐮𝐥𝐭𝐢𝐩𝐮𝐫𝐩𝐨𝐬𝐞 𝐂𝐨𝐧𝐯𝐞𝐧𝐢𝐞𝐧𝐜𝐞 𝐂𝐞𝐧𝐭𝐞𝐫 𝐭𝐨 𝐫𝐞𝐨𝐩𝐞𝐧 𝐨𝐧 𝟖/𝟐𝟔This newly renovated multipurpose convenience center will serve as the first multipurpose site to serve both Sevier County residents and short-term rental unit cleaning companies.

They would lease from me as normal!