Do you wish you could have went the ROTC route after Basic training?

I was enlisted prior to going through ROTC. I can tell you that the "know-it-all" attitude is not a cadet thing. It's a military thing. And it's probably a human thing if you want to get right down to it. Most of the guys in my ROTC class looked up to those that had prior service and rarely did anyone try to play stump the chump with us. I don't know what all you have done so far in your time in the NG but you are probably not much father along than cadets. I don't mean that to be insulting, it just takes time to acquire experience and you've had little time to do it. You'll have more time in some areas than them for sure, but not a lot probably. Plus, you've probably received very little training as an E-2 in things like writing OPORDS and whatnot. So if the officer thing is something you're interested in, don't let learning with cadets get in the way of that.

No the two best jobs in the Army: Squad leader and First Sergeant can not be held by ocifers only Sergeants get that honor.

I learned a lot and had a lot of fun during my enlisted days and I wouldn't trade it for the world, but I do wish I would have commissioned earlier in my career. I'm around 16 years total time in service but I only commissioned a little over a year ago. I'm more than a decade older than many of my rank peers. If I could do it over again I would have commissioned after I got back from Iraq in 2004 when I was young buck sergeant. A buddy and I actually started to get our packets together at the time but I didn't go through with it. I lost track of him over the years but he's probably about to become a Major while I'm a butter bar. Of course if I went that route I never would have met my awesome wife and she's easily the best thing to ever happen to me so I guess it all worked out.