Quote from @Andy Sabisch: Question . . .our leases have a NO SMOKING INSIDE clause. 

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.

Having a lease from someone that has no authority to lease the unit does make them a tenant.  

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.

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

I have REPS status, but currently rent this particular Property to my Property Management LLC that leases this home "from" me and and pays me 5000/month rent as shown on my soon to be Schedule E.

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

It's difficult to see how a tenant will be after screened and signing a lease.

If you can rent it out, get it rented out, get a year lease, then start approaching commercial lenders for either a DSCR loan or a 2nd mortgage, with cash out. 

Master Lease with Option.