Hi members, hope you'll have some advice for me... For the last few years I've helped my brother (he's in his 50's) emotionally & financially. I've purchased for my nieces new wardrobe for school, summer, winter etc. I've given him several thousands in cash just to help him out. Aside from helping him, by now I've lend him over 10K. My siblings & I own a house in nyc & he lives in one of the apts rent free. My question is, if I give him an 'invoice' for the cash he owes me would it be valid & legal? Can it be deducted from his share when we sell the house? I don't know how I can get paid that cash back...

You trouble is nothing in writing, he can claim it is just another gift, how are you going to prove it is not.

You need to get him to agree to an installment payment plan and sign some paper work on it.

"valid" "legal" yes and no, it is not a item to invoice, it was a payment,
Do you have copies of the check or checks given to him, proof he cashed them and so on.