The challenge was balancing the relationship between landlord/tenant and a personal/friendly relationship.

It may be more difficult to get financing and a good rate buying through an LLC. 

@Diego L.That's actually an interesting situation and a case where revocable trust may make sense.

I hear Dave Meyer sometimes talking about Green Bay, Wisconsin and a few other markets on the podcast where he's saying you can go on Zillow and find some deals that are cash flowing.

I currently own two properties - my primary home and a vacation home in Truckee we rent out on Airbnb. 

So I changed my approach from slacks and a tie and "Hi, I'd like to help you sell and buy" to shorts and casual - but nice - button down shirt and "Hi.  

As a result, we have significant water damage to the floor and rugs in that 2nd floor bathroom and a bedroom, plus there is even more significant damage to ceilings, walls, furniture, and rugs to 2 bedrooms on the first floor.Our initial goal is to dry as much water as possible with wet-vacs and dehumidifiers.

I don't want to discourage you from pursuing a graduate degree and a promotion but if you have a passion for entrepreneurship I would encourage you to lean into that instead.

This comes down to need and a plan.

So even though I lost a deal and commission I won loyalty and a client for life and became very valued as an agent and very successful by getting the money that was deserved and obviously, rightfully, morally and legally due to her.