Complicated finances, different decision-making processes.

We'd do some work ourselves and hire out some work to manage the budget & go at our own pace, and we'd live in our RV during that time. 

I am in process of purchasing an investment property in New Jersey. 

This would require hiring an attorney and create some long-term obligations, but may solve a number of your problems.  

I'm in the process of doing something similar but I was looking to do a ground-up project in the Hudson Valley.

Would you suggest hiring a property manager or run it myself ?

I want to develop a process, but don't want to waste time with gathering research points that are ineffective.

Only if a potential tenant passes and we want them to sign a lease do we start the process.

But they will generally not simply outright lie.What you can also do is go through the process of inquiring about placing an offer.

I went through the setup process meticulously like 5 times, and it says everything is fine, support thinks everything is fine, but I don't get any booking.com messages in Hospitable, nor do the automated messages get sent out.It seems like quite the hack/workaround they have set up with booking.com so I'm wondering if it really works reliably at all.