If they are taking the risk of borrowing they would want to charge you a premium for the risk they are taking. 

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

As it relates to lease end dates I've seen two things work here. 1) You can stagger end dates as mentioned above or 2) you can optimize for summer - this works better for us in areas where you see students or families with school age children moving to align with the summmer months.Separately, this is a great argument against month-to-month leases.  

No I would not go with a company charging that.

Quote from @Ashish Acharya: @Sanjai Dayal If your LLC owns the commercial building and leases space to your medical practice LLC, it’s essential to charge rent at fair market value (FMV) to avoid IRS scrutiny.

That amount is baked into the rent you charge.

(income = 3 x monthly rent, Debt-To-Income, etc. can still be used!)

For the next billing cycle they increased my charges by $500 and did not notify me of the upcoming charge.

I have 16 homes in Rio Grande Valley that are RENTED for $1000 plus per month.

Mind you, they had my plans for months.