you can obviously... be patient and just save up from your active income. 

I figure if I start out with a low maintenance property, I can lower the learning curve and decrease the stress of managing a business and rental property myself to allow me time to figure things out as I go along. 

Walking back an agreement where you split the mortgage 50/50 and he pays utilities may be difficult and could stress the friendship. 

You need to establish a relationship with an active agent closing deals month to month.

Questions for later: • Is the high level of activity an overreaction to a nonissue?

It is possible that you could take the deduction for your rental as a separate investment activity. 

Based on what I have heard/read thus far, it seems like I don't need a formal legal structure such as LLC for running this is as an active business (but I may set up an LLC for asset protection, which is allowed by my mortgage lender).

Sometimes a pestering police presence can be a deterrent.If the suspicious individuals are engaged in criminal activity, calling the police while it's happening helps too.

The investing life before Jake was difficult, lonely, stressful, overwhelming at times.

I used to be active on here (BiggerPockets) around 2009, and wow, how it has grown!