I figure if we do good at that, then we can be forgiven if we make mistakes down the road and mistakes will happen, that is simply the nature of a business.

Right now I'm leaning towards managing myself, but would like to gain some insight from someone that has managed their own property from afar.Also can anyone recommend a good property manager in the Hampton Roads area just in case I do decide to go that route?

I know the place youre talking about and there are also multiple MF properties for sale on the road at favorable or decent prices.

Stay away from Noble road unless you are personally running the property as a hands-on owner.

When an investor believes that debt won't matter as it's paid by tenants, or just as long as you can make the payment, they can be on the road to failure.

Biking/ kayaking road trip), then found that life was kind of boring with no purpose other than recreating, and got my RE license and started helping others in order to have something to do.

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.  

It can be easier to sell SFR down the road and they tend to appreciate faster.On the flip side, however, finding a good duplex and a good dependable tenant can significantly offset ownership costs.

Your landlord seems to be violating some tenant privacy issues for sure.And, once you start down this road, you probably want to be ready to move as he may not like it.

Sometimes (usually) this means they don't have employment so there might be other problems down the road.