Hello fellow mustachians:
We are about to make a large purchase for which I've been saving for several years. The purchase price is $65,000, and I currently have a brokerage account to cover this purchase that totals $96,000. Some of this money is in cash; as the purchase grew closer I just put money into the account and didn't invest it, so I have $16,000 in cash for the purchase. I need to sell ~50K to cover the rest of the purchase. I would like advice on the best strategy for this.
Question one: Should I sell stocks that have been losers first? Does that balance with my winners to minimize my tax burden?
Question two: I have a large amount of money in an index fund. I bought shares in this at several different times. When I sell this, are the taxes based on each "bunch" that I bought, or on something else? Is it worth it to talk to the folks at Fidelity (where the account lives) about a strategy?
Question three, and excuse my naivety : I know I need to pay taxes on this, but I am wondering if I can figure that out in Turbo Tax and pay it on the next quarter, or if it's worth getting an accountant to do this.
This is the first time I've ever sold stock -- it's odd to think about using money and not just saving it. Any advice for a newbie on selling stocks would be appreciated!