If I could get any advice on how to get more familiar with the scope of work needed for rehabs this size or what the procedure was, maybe shadowing somebody I would feel more comfortable in moving forward.

I'd leave sealed containers, but anything that's been opened I'd either throw out or keep for myself if I felt comfortable doing so. 

Of course, we never know everything and so it becomes an easy excuse to do nothing and remain in our comfort zone.The "right moment" is now, Cynthia. 

It's too close for comfort.

I feel comfortable speaking with the owner, but have offers below his original asking price.I would like to meet him again and give him my offer that he is sure to refuse.

Getting comfortable with a Sponsor takes some research, but is a good way to set up passive streams of income and benefit from property appreciation upon sale of the asset. 

Style will end up taking a back seat in those situations.

I know others do great with them, but it's not my comfort zone.  

Always consider the "worst realistic outcome" and make sure you are comfortable with that.

If you do not feel comfortable walking in that gray area, I would think about just doing a traditional rental.