1. "A Type "D" pick is the result of a franchise not being able to sign a non-supplemental pick from the first 3 rounds of the previous amateur draft. In order to receive Type "D" compensation, you must offer the draft pick his initial demands, he must refuse to sign the contract, and the contract must never be withdrawn at any time during the current season. If you are unable to sign your first, second, or third round draft pick you will be awarded a compensation pick in next season's amateur draft. The compensation pick will be at the same position as last season plus one except for unsigned third rounders in which a supplemental pick is added at the end of the third round." The language "not being able to sign a non-supplemental pick" means that the 25th pick or whatever acquired by losing a type-A is eligible for type-D in the following season if player does not sign.
2. Correct, and correct
3. No, very conservative for supplemental only applies to 1*
It's wise to do "Very Conservative" for the supplemental round so that you never lose your supplemental round picks for nothing. You might sacrifice a bit of value in exchange for asset certainty. Also it's useful when you first begin your rankings to Ctrl-F for "probably won't sign" and then move all those guys to the bottom. Or you could be a gambler and sometimes you will snag a guy that all the other teams passed on based on their settings. It's rare, but it can happen
Player Profile: Louie Kondou