It is always interesting to see the various styles and procedures of individual divers. I have no problem with negative entries. In fact I rarely hang out on the surface on any dive. Short of air off or not enough weight, I can think of few problems that can’t be taken care of at depth as easily as on the surface. Some, like bubbles from a leak, will not be obvious until submerged.^^This. I've done negative entries before in Coz. I didn't understand their need, why didn't the boat just head a few hundred yards up current and allow us to splash, as a group, with some air in our BC's?
Part of this is probably experience, I have been diving long enough to know my weight. And knowing and maintaining your own gear so you are intimately comfortable with it. Plus checking your rig throughly and several breaths before splashing.
Also experience gives me an advantage to deal with issues at depth. Knock on waves, I have never yet had to return to the boat early to deal with a gear problem. I have had on occassion to get some help from a fellow diver/buddy.
As to need, I am no boat Captain, but it seems reasonable that the further upsteam from your target, the more likely to get push off it and miss it completely, espcially if you are unfamiliar with the dive, reduced viz or no easy landmarks. And floating on the surface may well carry you off target.