1. If they are on the bottom of the D1 list you should have a shot.
2. Yes... sorry, but its situational in many ways. Some players never drop, even if they give you the backup message. If you believe someone else will covet them acting early may e a benefit. However, with limited ships other coached will know you don't have much budget so you can probably be easily defeated if they DO want the player, so perhaps waiting to not only see if he drops but to gauge other interest/risk factors could be good - its variable...
2a. again, maybe. But pulling down someone from 100 miles or less should cost less than a couple grand, so it ought not to be a massive amount...
Not sure if this link helps at all or if you've seen it before, but in case its relevant or helpful:
HD Pulldown Advice.doc - Google Docs