A computer-implemented method and system to facilitate a purchase by at least first and second cardmembers using respective transaction instruments associated with a single tax-advantaged account. A request from a merchant to charge a purchase by the first cardmember against the tax-advantaged account for a transaction using the first transaction instrument is received at a host computer. A determination is made whether the first cardmember charge is for a covered tax-advantaged expense. The tax-advantaged account is credited with points associated with the value of the first cardmember charge only if the first cardmember charge is determined to be for a covered tax-advantaged expense. A request is received from a merchant to charge the second cardmember against the tax-advantaged account for a transaction using the second transaction instrument. A determination is made whether the second cardmember charge is for a covered tax-advantaged expense. The tax-advantaged account is credited with points associated with the value of the second cardmember charge only if the second cardmember charge is determined to be for a covered tax-advantaged expense.