"Ideally I would sell my most expensive shares at that point keeping some shares just in case."

PTSCer,

Not knowing your particular situation, here is something that is automatic with Fidelity........

I have bought EDIG from 2000 thru 2003, laid off until Sept, 2008 when I started buying again, with my last buy Oct 5th, 2009.

I hold EDIG in 3 accts, and when/if I begin to sell, their default for each acct is "1ST IN, 1ST OUT." I e-mailed them last week to confirm this, and anything held less than exactly 1 year is short term, and 1 day past a year is long term. These factors effect cap gains/taxes.

I believe this to be standard policy by all firms, but check to be sure.