I chose a different strategy; accumulate monthly and sell shares when the reach 50% short term gain and/or 25% long term gain counting matching and dividends. IOW, dollar cost average the money in and sell at the peaks. I've never had an ESPP that allowed anything other than twice yearly purchases on set dates. If it were possible for me to buy monthly instead, then I would most certainly do that. You're fortunate that your employer has the plan structured in that way. I'd love to have one like that.
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