The rehab essentially gets "deferred" until a later date.Since most of what I need to do to this property is outside the house, it would give us some cash flow and let us do the exterior stuff a bit at a time around our busy schedule.

I would recommend just getting your contractors in there to inspect and put together your scope of work as opposed to getting home inspection after closing.Hopefully you won't find anything unexpected and the numbers will still work.

Her main reason to sell it to me is because she would be able to stay in the house with her animals as opposed to moving into an assisted living type place.I think it is a great way for me to get my feet wet in real estate investment.

As does exterior paint and facia.     

And at what point does an up and coming neighborhood become a good investment (as opposed to I buy now and it becomes a good neighborhood 10 years from now)?

The problem is that the inspector has no clue concerning the foundation and how the rest of the exterior walls are connect to the existing structure without approved plans submitted in the first place. 

As does exterior paint and facia.

I would recommend looking at vacation properties that are more reasonably priced as opposed to something in Breckenridge.

Or hard money loans, which many times is explained as "cash" because it funds quickly (as opposed to a mortgage with a bank). 

I think you need to avoid placing the signs in the "right of way," as opposed to private property (possibly minimally maintained) that happens to be near a street.