I think we have rules about these things just to keep some sort of consistency. For me it seemed to come up with the debate about death. It seemed that there were 3 paths suggested at the beginning of the game : 1) nobody dies (David Von Erich as world champion in 1987 ... creepy) , 2) deaths by some sort of random selection (sorry, buddy, Ric Flair just died ... also creepy) , or 3) death happens as it did in the real world (by sheer coincidence, David Von Erich is not locked into a big match at the time he dies ... weird, but workable). In the end, the decision was made : dead is dead and retired is retired. If it helps, think of it on the Final Destination principal : the wrestler might escape this particular death or retirement or catastrophe in this timeline, but ultimately, it will find them
As far as pushes and angles, it seems to be a matter of particular taste. Part of the fun of it, for me, is using as the unvarnished, raw talent they are in some cases. I certainly know I have been one guilty of giving people gimmicks or pushes ahead of their real life status, but I try to keep it clear they are doing it as rookies, and pair them with more experienced hands for guidance. That is one of the reasons I have been shy about having a singles match with Scott Hall and Dan Spivey, even though the angle seems to be heading that way. In 1985, that would have been a pretty rough match.