You will be a millionaire by age 30.

Most likely, I will contribute to these expenses with my own money but I plan on opening a separate bank account for anything related to the house.

If the wind blows heavily, I used to live in Houston and now in Colorado-both high wind areas, it can easily peel at least several courses off.Low wage workers, and let's face it roofers are relatively low wage, are NOT CAREFUL in their work habits.

For investments that are relatively static and singular in nature - shares of a private placement for example - the services of a self-directed IRA custodian can be sufficient. 

How does a relatively newer solo-investor compete with these types of owners/investors who really don't seem to care what they make - and are just plopping down cash all over the place?

They wouldnt even consider another loan program I was asking about to purchase a house for my aging father.  

“Large” tracts in or near Raleigh is a relative term.

The 1st story has one tenant, a locally owned and operated clothing store under lease through 2019, that caters to the younger college aged crowd that attend the 2 local colleges.

The license law is that you have to be at least 18 to be licensed and I presume you can take the course work at any age. 

It takes time to review the financials, inspect all the buildings, the infrastructure, talk to the tenants, perform a Phase 1 ESA, discuss with the city any zoning / code violations or other chronic issues they see.