Could it greatly increase your DTI ratio?  

As long as you pick the right areas in San Antonio, your rental will do well and your rents will continue to increase year over year.2.

It is also going to increase the amount you are paying every month in mortgage payments (aside from the PMI). 

Its clear that we will need to find a way to increase the occupancy rate, to be able to make profit.

I don’t remember the timeline off the top of my head but it’s a simple Google search to find out.

Seems simple if they don't want to sign, then this tells you the problems you're likely to face in the future. 

I want to keep things as simple as possible so my questions are:1) Can I simply make the agreement between the renter / Lessee and the Management LLC/Lessor or do I need to reference that the Management LLC is acting on behalf of the Owner LLC and state the name of that Owner LLC in the lease?

Step one in optimizing your listing might be to set up a simple website with a landing page, event calendar and blog so you can become the hub of information for people traveling to that area. 

Short term rentals impose costs on the local community (parking, noise, increased demands on infrastructure), so regulation is completely justified.

I am a long term investor (hold or perpetuity) so I am confident over time cash flow will slowly increase as will appreciation.