The biggest thing to keep in mind about taxes is w

The biggest thing to keep in mind about taxes is whether your stocks are subject to short-term capitol gains (STCG- held less than one year) or long-term capitol gains (LTCG held for just over a year);

For single taxpayers, STCG will be taxed as ordinary (earned/work) income (= higher taxes) and you might have to pay as much as 37% taxes for big profits.

For (singles) and LTCG and profits of less than $200k you would pay only 15% tax. For $200k-$425,801 you would pay 15% + 3.8% (net investment income tax) = 18.8% tax. For LTCG profits above $425,801 you would pay 20% + 3.8% = 23.8%. 23.8% is the top tax level for LTCG.

If you have LTCG stocks (and you can live on a mere $200k per year), you might be wise to keep your LTCG taxes at 15%. This is what my tax man advised me to do (keep profits at < $200k per year).

In addition, there are state income taxes to consider. Some states tax capitol gains profits and some do not.

However, if there’s an SFOR buyout, you may not be able to control your profits in this way.

I hope this helps.