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My 21 year old son will graduate from college next May. He is in need of significant dental work(orthodontia and then implants) that can't really be started until after college when he will be in one place for awhile. This is not the result of an accident or injury. It needed to wait until he was done growing as well. He has already used up orthodontic benefits from the dental insurance that currently covers him.

My husband and I have told him we will pay for this. Unless there's a better way, we will pay the drs bills directly. Because of the dollar amount of his college bills for the first half of '06, it would probably be easy to make the support case for him being our dependent for '06. I need to re-read the pretax account definition of dependent to see if we can at least cover some of the bills with that.

Are there any gift tax issues if we pay the bills directly ? Should I run the scenario of married filing separately with me(who makes significantly less and can somewhat control my income) taking him as a dependent to see about the misc medical deduction ? Anything else I should be looking at ? I suspect(we don't have the final plan yet) we are looking at $25-$30K, possibly spread over 3 or 4 years.

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