1. It is hard to tell: your 'toughest' win is against the 12th ranked team and all your losses were from teams that are playoff bound. I guess it's hard to tell right now. The next few games will define if you guys are contenders or not. Your last leg of games are mostly with teams who will be pursuing for that last 8th spot in my opinion. Good luck to ya. My projection is that you will lose to the top 7 teams and win out the others and will still retain the #8 seed.
2. Only halfway through the season and your guy is in position to take the lead, but you're not leading by a significant amount. I say you will finish it due to your high level/mismatches, but I don't think it will be a blowout.
Off topic: my own guy, Chase Harrison, is on pace to be the leading pass rusher for DTs. Not to toot my own horn, but I'm a Bears fan and my guy reminds me of Tommie Harris, so go Chase!