I’m contemplating having her give a security deposit and allowing her up to 4 weeks as a week to week tenant and requiring her to get renters insurance, pay up front, and give the dog up to be able to find a rental.

I'm contemplating on sticking with NoVA.In your opinion for the following neighborhoods / communities, how would you rank with respect to: rentability, low vacancy, quality tenants, higher rent, more desirable?

I love Montana, Gardiner, especially & am contemplating purchasing a house near the YS river and in town.  

We have $60k in the bank and another $100k in HELOC lined up and waiting.What awesome advice would my fellow BP'ers have for us as we contemplate dipping our toes into house flipping?

The fact that you've actually done the analysis and are now contemplating doing a deal because the numbers make sense as opposed to "a gut feeling" is a huge advantage in your favor.  

Coveted holdings that scream hold me for a very long time.I'm in a similar boat in SF and NYC, and have contemplated a 1031.

I would check with the local rules in the area you are contemplating purchasing a foreclosure in (5 Burroughs) and find out what if any tenant protections may exist.

The temptation to walk away and lose whatever is left of your equity will become overwhelming.If you are contemplating any strategy, like flipping, that requires you to time the market, you must also be very careful, because the market can turn very suddenly, and you don't want to be stuck with a half-renovated house that you can't sell and that is producing no income to you to offset the construction and carrying costs.  

A lot of the important aspects of investing in RE is local knowledge, and I knew that though I was not a rock star investor, I could still give back valuable insight to others that were both in my market, or contemplating getting into it.

What you are contemplating is scaring the crap out of me.