I have one rental property that I have been self managing for about 10 years but I'm looking to exploring and potentially doing my first Flip this year. 

Do you recommend making relationship with property management companies?

@Chanel Snerling if you're going to rezone in those Neighborhoods, you'd be better off going with max number of units possible.What construction project development & management experience do you have?

Then pay them a fee for finding the deal and pay them 8-10% of rents to manage the rental(s).

Are they way under market, or is it manageable for now?

This will save you time and effort, as you won’t have to travel long distances to manage different properties or handle tenant issues.For your first investment, I suggest starting with 2-4 unit properties.

It depends on the property.... is it value add where there's also a construction component or merely a management improvement opportunity?

Do you plan to manage yourself or will you be hiring a property manager? 

Assuming that continues and you manage your properties competently people will think you are way smarter than you are in 10 years. 

I manage hundreds of rentals and have had thousands of tenants, but I've never been sued once.