My first REI deal wasn't the best and it was a tough road on that property.

Find a good property with strong "guts" that doesn't appear to be a money pit, and get your feet very wet before considering fix and flips down the road.

In places where one can buy a house down the road (e.g.

This will work all the way to end of the road.

Also, you set the tenant's possessions on the side of the road and anything worth keeping will disappear within 24 hours. 

That means take into consideration vacancies, maintenance, property taxes etc to make sure your not negatively geared ( losing money each month on a leveraged asset) hoping appreciation will save you down the road

Obviously the initial thought is replacing one roof rather than two, but other than that, in my opinion, the two single family homes have a better chance of appreciating quicker if I decided to sell down the road.  

Make sure it isn't land locked (it has direct road access) and you'll have yourself a deal that a land investor would pay for.As for your thoughts on how to value the land based on highest and best use, I'd say that most land investors are flipping and not improving or splitting.  

I live in 27703 and my neighborhood is very low crime but a 10-minute drive down the road can get into some sketchy areas.

There are plenty of people on BP that are active in the Hampton Roads area.