@Mark Dahl could go down a huge rabbit hole on this one but keeping it simple here's what I look for personally. 

@Lee SyndergaardFirst I would make a list of all my assets and the way they are titled (bank accounts, savings, brokerage, retirements account, properties) and their value.I would bring also copy of will, living trust, advanced directive, and other documents regarding estate planning.Then I would also have a simple financial statement of the different investment properties and bring a copy of the lease agreement and insurance policy.The different topics that you would probably want to discuss with your attorney would be:Your estate planning,Your asset protection,Your real estate operation in regard to tenant selection, lease agreement, tenant eviction, security deposit holding and return, advertising regulation, licensing requirement, insurance.

To avoid situations like this, we have a simple eviction policy that is explained to tenants upon move-in.  

Hi Devin, You can start with a 203k loan if you want a simple process that can walk you through all the steps along the way.

My questions may seem simple but I fully understand its complexity: what is the best way to make this happen, what direction do you recommend for the refi cash out, what strategy to utilize to help guide me on this journey of educating myself and building confidence through working in notes and multifamily acquisition and ownership?

Bonus if it can be turned into an educational how-to guide.The resident can either pay out of pocket for any work needing to be done, or they can let the GNA cover it in exchange for direct principal payments off the original market price purchase.Make a simple guide to what needs to be done on a regular basis, and establish a plan for what the resident can handle, vs what the GNA provides.Create synergy with kids and grandkids to accomplish common/ regular tasks.Opportunity for daycare/ day camp, or even homeschool type services.Opportunity for future continued business partners to take over living on the residence.Preferred scenario, resident pays for material and professional labor, and the GNA provides cheaper labor for easy tasks etc.Residents may pay part of the labor cost, but ideally if the GNA has cash to pay internal employees, then those costs get applied as principal payments.Explore options that let GNA employees trade time for ownership of that specific property, instead of traditional pay, or use it as an overtime bonus.Find ways to incorporate local artists and craftsmen, and make unique projects that incorporate the story of the house as told by the resident.

Looks like you were able to keep it to simple cosmetic updates.

Doesn’t take a lot, of no existing liens then it’s pretty simple.

The bathroom is very basic / simple as well as the kitchen, so could perhaps modernize those a bit.

So my real estate story is simple.