Hi: Jamie, hope you're doing well.

It seems like you have some very solid goals of multiple income streams, and a well calibrated risk tolerance. 

Of these professional wholesalers, nearly all of them will be well capitalized professional real estate investors or large businesses doing hundreds of deals annually with many years in and around every part of the real estate investment journey.

First time investor, hoping to obtain my first duplex soon, and this family land purchase is on the horizon as well.

Lots of areas that pencil very well on paper but the quality of renter you will get is going to eat into any profit you may think you are getting.

Well duh, because that motive to alleviate the bad is gone. 

Selling an existing, well-performing asset has some risks.  

I highly recommend a well-qualified REALTOR who works with investors and knows how to help you best.7.

Those remote flips and high cash flow rentals are so tempting on paper, but they rarely go well in reality. 

*I know the markets really well even better than some local agents.