Another factor I considered is that the role will help me understand RE markets better and be looking at a lot of deals.

I have been playing the multifamily game for almost 10 years now, and the GRM is one of my least favorite methods personally since it ignores so many important factors (steam boiler versus electric baseboard heat as an example). 

I am concentrated in the land development sector and multifamily.

Of course the goal should be on the first page by anytime but that is usually bad ROI since the price is the biggest factor on the rank.

what factors should I be looking at when making this decision.  

Oh also number one skill to develop regardless of the route you take is being able to identify and get in contact with motivated sellers.

Areas with new businesses or developing infrastructure often show good potential for flips.Next, building a solid local network is key.

It could certainly be a concern - but depends on a lot of factors - are you looking multi or SFR? 

There are markets that have built in "gotchas" like the rising cost of insurance in coastal FL, regulations in much of the west coast states and property taxes in Texas; however, the deal itself is the most critical factor.

Quote from @Steve Lehman: @William VreelandAs a local Indy Investor and RE consultant I have been flowing the IHA development closely to see what kind of developments have been happening.