Being an agent will take a year or so to get off the ground so be prepared if you go that route.

Hiring a bookkeeper to watch the income/expenses is like hiring a gardener to tell you how many roof shingles are laying on the ground after a wind storm instead of hiring a roofer to repair the roof.I recommend that you look for a quality property manager who can maintain the properties and help with the bookkeeping.Start by going to www.narpm.org to search their directory of managers.

When you earn it from the ground floor like that, you learn so much more and can appreciate what you have.

I have seen properties get ran into the ground when being rented this way with poor management. 

You are creating a new job for yourself.With the number of STRs (I assume that just because there is 850 permits doesn't mean that they are all in use), plus the in you have with the other owners and the local page, make it easier to hit the ground running.Maybe you reach out to some of the independent contractors you know and ask them if they might want to join your team.

The key is to find a middle ground where you’re mindful of spending but still allow yourself to enjoy the present.

You're absolutely right, creativity is essential to make deals work in this environment, and building from the ground up, especially in high-demand areas like Raleigh, can be a great solution.Your current project sounds like a smart move, particularly with the zoning for a duplex and ADUs.

In my area , you would have a minimum of 1 year from the time you bought the land until you could stick a shovel in the ground .

They are the boots on the ground, the most important piece of the entire operation. 

For example what if a house burns to the ground?