He is going to be overpaid SSI for the month of receipt since the settlement counts as income in that month and it is over the SSI amount for that month. He will owe that month back so take it off the top.
These bills, are they his and your bills that you two owe? Or are they someone else's bills? Do you get regular statements for these bills or is this some sort of no written loan agreement that he or you have with someone else or is it money he has always owed someone for something they did a long time ago and now he wants to pay them back? How much proof is there that these bills are truly owed? Payment of valid debt is considered valid spenddown. Giving money to family because they always were there for your is not repayment of debt. It is a gift of money, a transfer, and SSI might penalize him for giving away his own money in order to qualify.
One vehicle of any value is excluded from the resource limit. How many will you have? What is the value of the second and third vehicles?
The SSI resource limit for a couple (and SSI knows you are a couple because you report your own income regularly, correct?) is $3000. Household goods, some kinds of burial funds, some other items are excluded from the resource limit. But if he and you have over $3000 from this settlement, the value of a second car and other money already in the bank as of the first day of the month following receipt, he will be ineligible due to excess resources and will owe SSI back for that month as well and won't be eligible until he is under the $3000 limit.
