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Although your son being self-employed may not be looked upon favorably by the mortgage lenders, the more important issue is their indivdual credit histories. If they both have good credit and not too much debt, then being married shouldn't really affect their chances of getting a mortgage.

The point during the year at which they marry doesn't matter for tax purposes because your marital status for tax purposes based on your marital status on the last day of the year. One thing I would strongly recommend is that they not by a house at the end of the year. There are two reasons for this: 1) they will only be getting one or two months worth of interest and real estate tax deductions and that may not be enough for them to itemize their deductions; and 2) if a taxable event occurs for them to get the money for a down payment (i.e. they sell stocks, etc.) they will get hit with the taxes on that taxable event and because of 1) above, if they can't itemize their deductions, they will be in a very unfavorable tax situation. However, if a house they really want to purchase appears on the market at the end of the year, it may be too good of an opportunity to pass up.

As for your other question, based on income of $50,000 and social securtiy of $17,000 your federal tax liability with the standard deduction an yourself as the only exemption would be about $12,500 (assuming no other income or deductions).

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