If you own either of the properties free and clear and don't need to access all of the equity to make the next purchase happen, that would be ideal.

If the residence is inside a gated subdivision or a controlled-access buildingthat is governed by an owner’s association, a letter from the association acknowledging the use and grantingaccess to occupants of the rental unit will be required as part of the application.A short-term residential rental requires a Conditional Use Verification (CUV).A short-term rental use is unavailable and prohibited within a residential unit or a room within a residentialunit that is located in an apartment building.

Quote from @Christopher Allen Main: @Nathan Gesner,     Looking at fileplace, is there a way to gain access to the full repo so I can download it all it for training my AI?

You’ll be able to access more equity in your primary vs a rental property, and the rate will be higher.

TurboTenant only provides eSign with the Premium version but it meets t$12.42/mo.

You could ask that they put a year or so of savings into a separate account on which you have view access or receive a monthly statement so you can see they have the ability to pay future rent.They aren't going to last without other income or savings with income at 1.25x rent.

The RE agent stated some properties on the river in the past did not get their lease extended to provide better river access.  

You should not have allowed access and now you are going to live the old adage of "it's easier to give slack later than to real it in." 

Also where can I access your extension?

Validate planning zoning requirements and access to utilities.