In my mind it seems that an easier and much more smooth transition into real estate would be to purchase the single-family home and rent out the extra room to my current friend/roommate.

For 15/30 minutes everybody involved in dispositions gets on the same page so every step of the process runs in a smooth and timely manner.

You will have to learn that things just won't go smoothly and you need to learn to roll with it, adjust and get your money going again.  

Once you solve those 2 obstacles you'll be smooth sailing ;)

Going on into the 2nd month and everything has been going smooth.

What they do want is a smooth transaction.John CoreyPS.

Hopefully closing goes smoothly.

I know the first time is going to be painful but I am keeping my hopes up that after the 2nd property this should go more smoothly but it looks good to me, but I would like some opinions, would this be considered a deal for you?

You could remove the end cap, fill with some Bondo/spackle/etc and sand smooth and paint.

I really hope my future first deal goes as smoothly as yours did.