1st question. Pokemon do not get weaker when you trade them. The just grow by 1.5 experience points. Thast's the only difference. They keep everything, Evs, Ivs etc...
2nd question. I am not an expert at Ev training, but I do not think it matters what level you give them Vitamins. As long as you do it correctly then you can max them out at a very low level. I think I got that right.
Master Mewtwo