[onlyrealcuzzo]

Interesting. Does your company not withhold shares for taxes when they vest for you? I thought this was required.

Meaning - your second option isn't really an option.

Your company withholds some shares when they vest (usually less than you actually pay in taxes). Then, regardless of whether you sell or hold - at the end of the year - the IRS comes after the rest of the "earned income" taxes you owe.

IFF you do hold the shares - for say another 2 years - you pay only capital gains on your stock appreciation for those 2 years (if there is any). You already paid "earned income" tax on the shares the year you received them from your company.