I've perfected my technique with the Hakko 808 now. The secret is to avoid touching the pads and just touch the pin and solder, sucking it up once you are able to wiggle the lead with the desoldering iron tip. For desoldering holes without leads, touch the tip to the solder. You should feel the tip of the iron sink and hit the board once the solder melts. At that time, suck it up and withdraw the tip. If you don't feel it sink down after around 1.5-2.0 seconds, try to suck it up and withdraw the tip. If it doesn't come up, add more solder and retry after waiting a few seconds for it to cool off.