That said, with it's cloud based model, I am able to find someone outside of my area and leverage their services.  

I am not looking for workarounds to get his deposit but rather to know how to give it to him and, apparently, trying to send it to him while he is in jail is the a viable option here and one that I wasn't aware was valid but it does hinge on me having to track him down rather than the onus being on him to give me the information.

Hi @Matt Devincenzo thx for vote.Sub2 is viable with the correct documentation.

Doing a nomadic strategy and living in it yourself without tenants and then moving out can also be a viable option to slowly growing your investments.

<sarcasm mode off>Now, getting you specific advice here is not realistic.

This is where it's extremely important to work with an experienced agent so you're not wasting your time vetting a property that wouldn't be a viable STR option. 

With funding plan in place it's going to narrow the focus of viable strategies, markets & properties. 

As you mentioned, pulling a HELOC on your current residence to use as a downpayment for the next property is a viable option.

If you can still cashflow on your current house with a home equity loan, that may be a viable option to have both!

This rental model is a lot easier as the tenants bring their own RV and are responsible for it's maintenance.