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As to your tax question by Jojo98

If you isolate just dividends, you could make (or just save up) an estimated quarterly tax payment for the dividends you make each quarter (div times marginal tax rate) You can get more complicated and look at gains and losses, and any other pieces of your income (sched C, rental prop, k-1s) that don't have withholding, and balance that out to determine an estimated liability on a regular basis (quarterly?)