I participate in my company's ESPP. Unlike most ESPPs, ours purchases shares on a MONTHLY basis, the price being the average on the last day of the month. A dollar contribution is taken out of each paycheck (semi-monthly) and used for these monthly ESPP purchases.
I've read a few articles discussing whether it's more favorable to hold the stock over a year to get the Cap gains tax rate, or instead, sell and take the 17.6% profit immediately. However, most of these articles address ESPPs that purchase stock every 6 months and price it based on the lower of either the offer date or the exercise date.
How would the math work in my situation? I've been holding the stock and the company has been performing really well, so I'm making substantial gains on the stock I purchased earlier... obviously less in more recent months since I'm buying in at the higher price. Overall it has been quite profitable so far, but I'm not sure the company can keep up the same rate of growth long term (that being said, I don't see it dropping substantially either).
Am I better off forgetting about taxes and just taking my profit every month right away or should I hold the stock and maybe sell off portions of it at different times at the cap gains rate?