I plan on getting into the flip game much once I establish a few rentals that cash flow.

I was of course intrigued by this process and soon realized that this was called wholesaling.  10 years later I have established my own business doing this.  

Ridgley's Delight is a well establish area with value that is likely to keep it's value or appreciate.

I think @Jay Hinrichs touches on the important point... if you can reasonably expect appreciation, then it might be a good bet/gamble. 

From day 1 I established a mgt co s-corp to manage my own portfolio.I use it very little the way you are outlining, though.I do not want to take beautiful SE-free passive income and turn it into active income. 

Take some time to establish relationships with agents, contractors and property managers in your market.

Then after I get some more general business experience and establish a track record of successful real estate investments I plan to jump into the self employment world and start scaling up. 

Talk to an accountant but my understanding is that as long as you have established residency for a certain period of time it is all of it.

@Kelly DeWinter  I know first-hand that the City of Annapolis requires unit to pass rental inspection to rent any unit in Annapolis, not just Section 8, and that we were not allowed to deny Section 8 applicant if they met our other established credit/background criteria unless we met certain exemptions, like an owner renting the house out short-term while they are away for several months (Section 8 requires 12-month lease). 

In my area, once utilities are provided to a lot, there is no hookup/installation cost to re-establish service after demo.