As a Legate in the Ordo Legionis, my opinion on the Imperial Jarls.
Jarl Elisif: Young, inexperienced and recently widowed. With proper mentoring, she could make for a kind and just ruler.
Jarl Igmund: Of all the Imperial Jarls, there is none that I loathe more than Igmund. I would afford him the opportunity to resign and go into exile, far away from Skyrim, then replace him with someone more suitable. In Markath.. not an easy task.
Jarl Maven Black-Briar: I've heard the rumours. Who wasn't? Influential and powerful.. but I don't trust her as far as I can throw her. I would oppose her being Jarl in the hopes that I can convince Laila Law-Giver to claim the title once more, as she appears much more reasonable all things considered.
Jarl Brina Merilis - A veteran officer with the people's welfare on her mind. In time, she will prove to be a fine Jarl.
Jarl Igrod Ravencrone - An interesting one. Distant at face value, but seems to have her people's interests at heart.
Jarl Balgruuf the Greater - No better candidate than Balgruuf to the Jarlship of Whiterun. Needs to make a pilgrimage to High Hrothgrar one more time though.
Jarl Brunwulf Free-winter - Capable enough, though his position is undeniably a difficult one. Regardless of competency, support will be required, all things considered.
Jarl Siddgeir - A lazy good for nothing, vain individual. Whilst not enough the kind of response Igmund and Maven deserve, if the steward of Falkreath can't make a man of him, then there are better options for the people of that hold.
Jarl Kraldar - Inexperienced, but is possessing a relationship with the College of Winterhold, which is of itself valuable moving forward even if the hold of Winterhold isn't valuable in of itself.