I'm preparing federal and California tax returns for 2006 through 2009 for a friend of the family. For Federal he owes for all tax years except
2008 where there is a refund. In aggregate, he owes plus failure to file on time, failure to pay on time and interest for 3 years which I have no doubt will be billed by the IRS.
For CA, he has refunds for 2006 thru 2008. He owes for 2009 plus any penalties and interest that the CA FTB cares to bill. In aggregate he should get a refund. However, for tax year 2007 the refund is unknown. He was assessed by CA and a tax lien was filed. His employer and he have both made payments. Some of those payments represent penalties and interest. The amount is unknown The tax return reflects all payments made and I assume the CA FTB will sort it out.
Here's the question: How should we actually file and pay these multiple years of returns. Should each federal return be mailed separately with payment enclosed with each return that he owes taxes? Ditto for CA? Or can he just put all four years in one envelope with individual payment checks attached to each year that a payment was due?