Microsoft ESPP Plan worth investing?

Aug 30, 2020 17 Comments

I max out my ROTH $401(k) contributions and plan to put a decent amount into my ROTH IRA. But in terms of more immediate return on investment I’m considering maxing or significantly funding the ESPP plan this quarter (up to 15% of income) and sell maybe half of that immediately to turn some cash over. Minus short term capital gains tax that should net me around 6% after immediate sale.
I’ll have to actually crunch the numbers to see what that is, but it would be around average YoY stock market gains. I already have significant stock from sign on bonus that i consider long term so I’d be using this just to make more short term profits. Are there more tax implications to this than just considering capital gains tax. Or are there other strategies people here use to leverage the ESPP plan effectively that I should consider also?

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