I would probably just keep the security deposits in the same new account that I would paying the bills with.

Please keep in mind, there is a minimum as-is value and loan amount.

You could try to have a flat hourly rate with them but in my experience, I like to do it by the job so that it keeps everyone honest.

In other words the generic limit of VA loans is $484,350 (if I'm not mistaken).The loan for $281k consumed $70K, mean you have about $50k that you can still use, or another house under $200k. 

It was built in the 1920 and is over 100 years old, meaning that a lot of big-ticket components are past their design life.

In high demand areas, more regulation can actually be a good thing in an STR sense - it means that they've accepted that STR's are going to be a significant part of the area and have established a process for how people can do them legally.

I live in one of the units, keep one as a classic rental and one as a mid-term rental.

Please keep in mind your bank will not likely allow the mortgage to be changed to the LLC name, however you can still transfer the title but be aware of the due-on-sale clause.  

Given the fact that it is possible to get stationed at the same base sometime in the future during what could be a 20,30, or even 40 year career some decide to keep the property.

This means cash flow is producing 4.3% ROE.