Company share scheme

With your trader hat on, if you could buy shares for a 15% discount of the average share price over a six month period. Would you flip them immediately and pocket the profit straight away?
Or would you formulate a strategy to sell a proportion and try to time selling of the rest at a optimum time?

The catch is that most company share schemes have a minimum holding period.

My employer offers a pretty good share scheme for each share you buy my employer will give me 2 more but the minimum holding period is 3 years.

Luckily, there's no minimum holding period. The only restriction is we can only buy twice per year and we can't sell 10 before the quarterly earnings announcement until 10 days after.

So it's easy to make a quick profit, but probably more profitable if I held on and timed selling them.
So far I've done a 70/30 split of sell/hold.

I'm not playing with huge sums here, but it's enough to pay for a nice holiday now and again, so I want to get it right.