OK Sorry for the delay. I did not do computer time today. Just enough time to return emails.
I have more questions. - Does he want to retain some owner ship? Is he just looking to have no house payment?
Total Value $660K.
Basis - $323K
Debt $66K
Liquidation Cost estimate 10% if he sells through broker - $66K. This can be less I just use this as a conservative estimate because the math is easy.
Cash Equity. $528K. So you should make sure he does better than that so it is good for both of you.
I can't stand Dave Ramsey because he advises people with out asking 100 questions that you should before you give advice like this. You really have to understand people situation a lot more before giving advice. I would rather talk to both of you for a hour and advise. I do deals with friend and family and they are loose because I trust them. So that has a lot to do with it.
Credit, jobs, income, age, married, plans for future all this matters. If he makes less 94K a year and married he can take advantage of zero tax rate which would come into play. You can structure the deal to pay him gains at a zero federal tax rate.
If he is ok with not owning the properties The easiest thing to do is buy him a house. He sells you his house for his basis $323k carries the note. He buys a house for $500K and you pay it off. Then you owe hime another $40 to $100K depending on how you figure it out. You and your husband gift him $19K each. If he is married you can each give him and his wife $19K x 4 = $76K in one year. Or hand him an envelope with $100K in it. People love cash.
He will be allowing you to leverage your money with his this is very good for you.
I am not a tax adviser and barely graduated high school so I am not sure if I would listne to me. There are a lot of ways to skin this cat.
If you don't have a great accountant which most are not. I have one that is awesome and smart and specializes in Real Estate tax planning mostly because he is an investor as well so he is really good at what he does.