I would imagine it would be wise to begin with performing because of the lack of risk, but I feel like if I had enough knowledge (which I currently don't) I would have no issue tackling a non performing one.

At that point you're an investors and know how to tackle the next one.

Hi David Sweeney ,I won't attempt to tackle the many questions contained in your post, but one thing to note is that since the subject property has >4 units, it is considered a commercial (not residential) asset.

I knew next to nothing prior to tackling this project, but thanks to Youtube, I consider myself very handy now.

I have done deals on both sides of the fence and unless you absolutely know what you're doing, tackling the GC tasks as part of your business plan are simply foolish.

Anyone in the Richmond, VA area been successful in tackling this?

If they do a good job i'll get them to tackle something at one of my properties.I've been bitten by lackluster contractors no risk/no reward

welcome to BP @Frank Mancuso , you are tackling it correctly.

If you're willing to tackle those two things you'll be fine. 

What do you want to tackle next?