I understand that most items associated with administering a will are not typically deductible, but this situation is a bit unique (at least for my usual work) and wanted an outside opinion. My clients father passed away a few years back and left a commercial property to his estate. His father and his fathers girlfriend lived on the property until he passed, and she continues to live in a home on the property while my client runs his business off the commercial land. The will states the property will be passed to my client 100% as long as he pays (from his money, not inherited funds) $2,000 monthly until the day she passes and then he will receive the property in full. He also fully upkeeps the property, pays the taxes etc. Should he not make these payments, she will receive the commercial property immediately and my client will get nothing, including being forced to move his business and she will immediately kick him out due to the usual discord after estates are handled. 

The question would be since he is paying her from his own funds, is there any recourse to deduct this or 1099 for this money as it was not being paid from funds that were in the estate. Rather, my clients funds so he can keep his businesses operating on the land in question. He obviously wants to give her a 1099, which she was originally ok with doing until she found out she would owe a small amount of tax by doing so.