With regard to the Social Security Benefits, having a blended rate of 20% for Federal Withholding Taxes may be more prudent in the long-run because your income tax is based on all income and not individually. So, for the additional income you are receiving from those benefits and the bracket it is pushing you up into, withholding a minimum of 15% to 20% on the gross amount (or the effective rate on 85% on the gross benefits, which is where the truly taxable amount is arrived at), would your best measurement of covering you by year-end.
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