I know I looked at the D2 list after about 20ish and he still wasn't on it.
That is not a reliable sign. Most of the time when I pull down a player, they never drop to my level on the search. That drop indicates a DROP down, which may or may not happen before they sign. I don't believe pulling down has an impact on that.
Are you saying players accepted the HV's before they were considering you?
Yes I've absolutely had that happen, although I think only with players strongly considering another school..not on an undecided player.
Also, are the players STILL undecided after the HV's?
Undecided players should normally/always be considering you by the time they start accepting HVs, but it is possible for them to accept HVs before considering you if another school is already way ahead.