My gut tells me that if I ran across a situation like this and knew enough that I was confident that it would provide sufficient cash flow, I would want to know that my other rentals could cover things in the event I totally missed my rent/quality projections. 

I would strongly recommend you get to an ARV that you feel confident and comfortable with as quickly as possible.

While I have strong confidence in my wife's friend, I also don't want to sell myself short in regards to finding a great home and think the 2nd agent has a stronger overall network.

I have been listening to the BP Podcast for some time now and never felt confident enough to start anything and now I am jumping in.

If actual, recent numbers.Exit Cap is forward looking and outside of a general uptrend in prices, is not real high confidence, especially the further out you look.I'd be more interested in NOI growth and how realistic it is and if your assumptions are sane. 

Initially, they were confident they had done enough to kick-start the recovery after our economy had fallen off a cliff.

Sure you might be a little more agreeable to go more on the higher end of your price range, if you are confident in being able to add those lots and occupied homes on them.

Developing confidence in knowing what is a good deal will come with time and will help you with "analysis paralysis".

My first deal was a house hack, although I was nervous about the process and uncertain in my ability, I was confident in the numbers.  

For what it's worth, I'd encourage you to work on putting some form of a plan together that helps identify all of these considerations and helps create some better definition and purpose (with or without a professional depending on how confident you feel about it).