As I grow I will hire a virtual assistant to take a few more tasks off my plate to allow me to live the same lifestyle. 

Yes, because Private Money infers that you are in a negotiable deal where your project can be outside the box and you can negotiate unique terms with a private individual - that - or a big box lender with strict rules and guidelines. 

You can take a deep look at the deals and get an idea of the kind of variety you'll see and come up with your own due diligence method (that meets your unique situation).

And I would say embracing the difference and performing at our best within our unique personality styles is the right thing for each of us.

Depending on your state and your business, you may have some unique and potentially urgent opportunities.

You'll likely find it easy to find people who will tell you what you want to hear, but you really need hard facts not speculation.But for some speculation, if you're talking about the Nantahala River or Little Tennessee, sure I think you might be able to do $22K/yr, but not much more, unless perhaps the places are uniquely styled. 

STRs have unique tax considerations, so setting up the right systems early will save you headaches down the road!

But, it's a unique strategy that requires more knowledge than expected.

I haven't done a 1031 exchange, but may in the near future and the small amount of research I have done on it seems to indicate that some qualified intermediaries only do the intermediary task (hold your money while you close on the new deal) and some try to do other tasks as well, like facilitate you finding the next deal, etc. 

Be confident, be courteous, and time will teach you what works based on your unique personality and skillset.