I'm fairly near the end of the first trial. I'm enjoying the story but the class trial has really made me not want to play anymore. I didn't enjoy the minigames in the first game, and I feel like they're even worse in this one. The (improved) Hangman's gambit isn't improved at all, it's just longer and even more annoying. This is kind of the same problem I had with VLR, where the gamey parts were often just an annoyance preventing me from getting on with the story.
The minigames will probably click with me eventually and won't be as annoying, I hope anyway.
I'm sure this will get modded and/or deleted almost instantly but I'm actually very dissapointed that most of the gaming press covering this have jumped instantly to the defence of these well known developers and condemned anyone complaining as a jerk or an asshole.
It's been so long since I played so I can't really give any specific advice but you should be using pretty much every role that's available to you.
Buffs and debuffs are key in this game, so you should have a paradigm composed of synergists and sabotuers. Sentinels have a passive damage reduction so if the enemy is winding up for a big attack switch to a sentinel paradigm to minimise damage. Commandos deal the most damage and slow the stagger bar, so it doesn't immediately diminish. Ravagers are best at staggering the enemy, which is key in every fight, so switch between commando and ravager roles to prevent the bar from quickly draining.
Going to be blunt here, if you want to ask her out then you just need to do it. Stop posting twenty times a day about it here and analysing every word or look she gave you and just do it. The more time you spend awkwardly hugging her or trying to call her late at night the less likely I think you'll be in successfully asking her out. This is time that could be spent touching her shoulder. If it fails remember you can always fake your own death, chicks love that.
I'd recommend Ultra Street Fighter 4. That game still has a ton of people of all skill levels playing. It's also relatively slow paced, so bar a few characters you won't feel overwhelmed and completely helpless. If you want to eventually play more fighting games the skills you'll learn from USF4 will carry over much more than things you learned in a game like MK9.