I am in the process of obtaining a divorce. My soon to be ex wife made the choice to file taxes married seperate. In which she has filed her taxes and taken all deductions. she makes just enough to pay her first mortgage and I for the last 4 years have completely supported both her and her 82 year old mother. We were jointly common law married in 2007 and have filed as such since , up till now.
Is it legal for me to file a 1099 to her for the amount of money that I spent in the last year supporting her, her mother and her home based business? I paid all utilities, second mortgage and building improvments along with sevral thousands in legal fees when she got sued. the total amount I spent well exceeds her estimated income.

“Is it legal for me to file a 1099 to her for the amount of money that I spent in the last year supporting her, her mother and her home based business?”--->No, I don’t think so; in general, as yo can see, a 1099-MISC needs to be issued by your trade or business. You CAN’T issue a 1099-MISC Form just for your personal purposes. As long as you are self-employed as an independent contractor or you have your own business, you have to file certain information returns, 1099-MISC Form, with the IRS for tax purposes when you make payments for rent or royalties, and services rendered to your business by persons who are not your employees. These returns serve to inform the recipients of the income they must report on the U.S. federal income tax returns.