Our lawyer wrote up the loan doc, they borrowed $60,000 to renovate 123 main st, I got first position lien on 123 main st, they paid $500/month interest and the $60,000 lump sum back after 12 months.

My long term tenant (a family friend) is moving out and I am concerned how to make sure I pre-screen future tenants effectively without violating any laws. background: this property used to be my primary home and had a very informal agreement with a family friend to rent from me in the mean time.

The initial tenant issue was settled at $700 and change, which I paid.

I have had multiple buyers over the years not pay any closings costs and only have to pay for their down payment because the sellers paid. 

You pay in two ways:  Upfront cost and in pre-payment penalty. 

At court make sure its said he didn't pay/paid late, you didn't renew and he is still there.

Quote from @Aaron Zimmerman: @Justin Cummings - congratulations on building a nearly paid off portfolio.

Now, if she did that in a prior year, you technically would have paid less taxes than you should have and will likely need to amend your return.

we do a brief pre-application online before offering to physically show any apartments. 

The Airbnb paid for almost all the expenses of owning the home and my "rent" was just putting $200-300 away each month in savings for maintenance and capex.