I appreciate your feedback.

I am in a position pretty similar to you, (freshly) 25, finished up college a little over a year ago, and looking at getting into this in the next 6 months and move to the Winchester, VA area.

Does anyone know of a great property management company for a "D" property that could provide some good and honest feedback for my units?

I have about 150K to invest with the same amount in reserves (but could be used to increase my position).

-how would it positively affect me?

Based on the feedback, it seems like I have nothing to worry about. 

What positives and negatives have other people found while pursuing the BRRRR strategy in small towns?

If the triplex has equity, tap that to purchase addition cash positive earning property.If the Triplex isn't cash flow positive, then that would be the time to think about a 1031 exchange into something that is cash flow positive.Everyone has to think about their personal goals when investing, short term and long term.

Any feedback would be appreciated.

I haven't read the posting at the link you provided, nor have I done this or any wholesaling either, but if this would be done by the wholesaler taking some form of equity position in the property, in lieu of collecting a wholesale fee, then I would think that this would be addressed in the deed showing the form of ownership as well as identifying the owners of the property (as well as some other partnership agreements/documents detailing ownership structure and management responsibilities).