I am putting $100 towards a mutual fund each month for my 2y/o daughter. The goal is to "give" it to her when she turns 18. (We also have a 529). If/when I decide to sell and cash out in 16yrs, how the heck do I handle the tax portion? If I'm buying every month, I'm thinking the tax stuff would be complicated no?
Your brokerage firm is required to track your basis on new purchases. Each year, they will likely send you a consolidated 1099, which includes dividends, interest and sales to be reported. If you make a sale, it will appear in the sale section, and they will provide you with the basis, the date of purchase, date of sale and gross sales amount, plus track wash sales.
It's not too complicated. Everything is tracked by their computer.