Thanks @TaxGuyBill  I going to give pub 925 a deep dive, I want the TP to qualify but I want to be sure I'm not just reading what I want to read to make it happen. I can't get past the fact that his real estate brokerage firm and his rental property are seperate, but his firm did handle the closing of the rental property he sold.....More to follow, I will get back to the forum, I'm not ready to run with scissors yet.