We have a current rental that a family member is interested in purchasing. Bought in '24 for $95, current value $160K. One thought is to sell home at the price we paid, saving transfer tax and helping to eliminate increased tax assessment which would benefit buyer. It would benefit seller in capital gains tax and transfer tax. The home is owned in our LLC. We are going to hold the mortgage for the family member. The remainder of the $65K that is owed would be paid directly to the sellers upon sale of his current home.

My questions.

Is there a better way to arrange the sale that would benefit us both tax wise.

for the remainder ($65) owed would it matter is the family member paid in the lump sum or should it be split into <$10k increments. what is the best way to shelter these funds.

I understand this is not a typical situation. My family member has the funds and is very trustworthy (employed, great credit, 40 yrs old, single) So we are not concerned that the payment won't be received.

What would you do

Thanks