This question arose because the IRS is questioning the taxpayers deductions for alimony on his 2005 tax return. The taxpayer prepared the return himself which probably wasn't the wisest thing but is water under the bridge at this point.
In a nutshell they are disallowing everything except for one $2000 maintenance payment he made by check. His mediation agreement which was entered as the parties' separation agreement and incorporated into the final decree stated that he was to pay his ex $2000 a month for 24 months months for a total of $48,000 in maintenance and a $22,000.00 automobile allowance. He was also to pay her health insurance premiums for a period of three years and was to pay her $7000 which was to be applied toward her personal credit card debt.
The maintenance payments were to begin in October 04 and the balance of the $48,000 (less payments already made), together with the auto allowance (less any payments he had made if she purchased a car prior to the sale of the home), was to be paid to his ex from the sale proceeds of the marital home. The home sold in February 2005. She had already purchased a car (in October 04) prior to the sale of the home and he began making the payments on it at that time and then the balance of the $22000 was paid from the sale proceeds. He paid $2000 maintenance in January 05 which they are allowing but they are saying that the balance paid from the sale proceeds of the home are property settlement and not alimony. He is willing to concede this because he understands their reasoning but believes he should be able to deduct the amounts he paid for her health insurance premiums, the $7000 payment and the car payments he made for her prior to the sale of the home since these things meet all the requirements to be considered alimony. He wants to go on and pay the amount they say is due ($25000+) in order to stop the accrual of penalties and insterest and then argue with the IRS about these things. Would it be wise for him to do this? I'm assuming if he does he would need to mark his payment as "paid under protest" or something of that nature.
As a side note, regarding the recapture issue, if the balances of the $48000 maintenance payment and the $22000 auto allowance paid from the home sale proceeds are excluded as the IRS proposes then his payments for the other things over the three years will be fairly equal and may not trigger the recapture.