This is a tax question for next year, not this one. I take 3 or 4 distributions from an IRA. Each time they ask me if I want taxes withheld but I say no. It's not a lot of money, less than $20k/year but at what point will the IRS start to penalize me for not paying a portion in advance? The ideal scenario would be for me to pay whatever I owe each year at tax time but I'm afraid they will fine me more than I would even owe for not paying taxes X amount of times during...