You'll need to tell us what your work clothes are if you want a better answer.

You'll likely need on of those ankle straps to keep your right pant leg from getting caught up and ripped up by the chainring.

I also commute in jeans, but for 2 miles it's not that big of a deal. For better or worse, I also wear Under Armour underwear which seems to keep any chafing from happening - I commute 3 miles to work. It's way more comfortable in my relatively baggy jeans, though.

I get sweaty in my 3 miles commute, but I could easily not get sweaty if I just wasn't 100% pushing my speed all the time.

I don't see why not!