Can I, or should I, approve both applications and then see who signs the lease first?

Investing in NNN lease (Walgreens, Dollar General, etc are your tenants) is also fairly passive, but you maintain a bit more control. 

With your background in lease management and site selection, that could be a natural next step.Regarding STRs, I can understand the hesitation—accurate expense tracking is critical, and not having that data can make evaluating deals frustrating.

On the other hand, if you write something into the lease that you agree upon, it should be fine, but that may turn off many prospects IMO.

The only thing I would mention here is you shouldn't have anything in your lease that a court would consider unreasonable, in case you ever need to go to court.

This raises a question because we had a lease agreement on file showing a rental amount of $2,000 per month."

Some types of Creative Financing include: Seller/Owner Financing, Land Contract, Wrap, Assumption, Subto, Lease Option, Contract for Deed.

Then you can take them off-site yourself so you have time until the next changeover or create another option for the cleaners that they go back and finish the sheets and store them so their changeovers will be easier as well.

January rent has not been paid to the property owner, as I am sure the lease spells out, but to someone else.

Longer lease term?