So, now very near the level 100 in speech, I went all around selling off potions and items to get up enough septims to train through the last five levels of speech to 100 with Giraud. But when I finally found him in Solitude (he only seems to show up at the Bard's college in the afternoon), he had no dialogue at all, just generic, "How may I help you?" types of pat phrases. I waited, I tried leaving Solitude and coming back, but still no dialogue. Anyone run into this problem?
training speach is easy. get caught pickpocketing or stealing something. draw then sheath your weapon and perswade the guard to let you go. with even 70ish in speach, he will. now find all the other guards, or most of them, in the same city. the more the better. easiest way is to find the barrecks. its tedious, annoying, but a sure thing.
dont worry about getting caught again by the same guard. just pick the top option about it not being worth their time and they'll agree.
you can go back after a little while to get the persuade dialog option in a day or less. rinse and repeat, rinse and repeat. easy peasy
Trainers cannot level you past level 90 if they are a master level trainer. This is to prevent people from training all the way 100 in a skill, aka exactly what you are trying to do. Make sure to take advantage of quests that grant skill points and the Ogma Infinitum. More information on trainers can be found on the `Trainers` page of the wiki, which can be found at this link: http://elderscrolls.wikia.com/wiki/Trainer_(Skyrim)