You would do better by developing a ongoing relationship with a mortgage broker rather than a specific lender.

We had to develop a filtering mechanism, otherwise I would keep chasing my tail underwriting every single deal that came to market. 

Read/consume, but eventually you have to make a decision and stick to it.

Items such as roves, HVAC units, and driveways eventually wear out .

A recent paid study showed that Gaston county had the best opportunity for growth in the region due to its infrastructure, plus Gastonia is putting major emphasis on growth and community development.  

Matt, if you are using VA loan you will need to stay on it but eventually, you could rent it out.

Are you trying to list the property for sale, buy existing property with income, or are you trying to buy the property and do a development deal on it?

Google "paint colors that go with wood trim". you will be surprised many colors look good with wood trim. if the plan is to eventually paint trim white, then I would go with the final color you will pair with white trim. why paint twice you know.

So assuming I will be buying more properties in the future, I will eventually be hiring a property management company anyways.

Yes I couldn’t agree more, the Home I purchased with my VA loan is in a great upcoming developing neighborhood.