re: Advice wanted on employee stock ownership plan

Any shares of stock that you'd had for over one year qualifies for long-term capital gains tax treatment, which of course means your tax rate on gains is considerably lower. So every so often (I picked six months, but I'm not strict about it) I sell whatever company stock I've had for over one year.

So if I buy shares through an ESOP with my paycheck every two weeks starting 1/1/2013, then for example fourteen months later on 3/1/2014 I sell everything that I'd bought between 1/1/2013 and 3/1/2013 (more than a one year holding period).

If your company stock has lost money then there's no need to wait but I usually don't worry about that and just observe the rule of thumb I've described here.