@Derrek J Hooyman I know you say you’re looking for a system and it’s never too early to plan for later by putting systems in place.

I might be starting grad school in Maddison and would be moving later this year.

Once you put something in writing as a proforma, I could see some buyer complaining years later if one of the years the numbers don't hit.

You might talk with a real estate/estate attorney and see if it's possible to open a probate, have a Personal Representative appointed and obtain an order from the court authorizing the sale of the property by the PR with the proceeds being deposited into the registry of the court for later distribution when all the heirs are identified. 

But later came back and said they knew of no other way to do it.  

We were initially looking to flip homes, which would potentially bring higher immediate cash returns for her enjoyment in her later years, however I’ve been researching the brrrr method as well to generate cash flow without the stress that flip process may cause her.

And buy & hold is a lot more forgiving than flipping: sooner or later all deals cash flow. 

Get a “Second home” loan and later decide you want to list it as a short term rental.

I think that people are so affected by what they hear/see when they are young, and if they don't explore their limiting beliefs and what they were taught, it will hold them back later on in life.

My question, do I wait and see if they will really leave by the 15th of next month or simply pay the $900 to start eviction now (which will still take about 6 weeks to get them out) I am concerned that if I pay the $900 and then they leave 2 days later.