That is a "classic" ORD BDL flight.
It's a gamble, that upgrade. I did it last week, and we sat on the runway for 2+ hours. The flight of course was 1 hour 55 minutes.
So in that case it paid off. I cetainly drank my 2 upgrades worth.
Oh, the other consideration is sometimes it's TWA metal, and 1st is the only part of the plane with power ports.
As to BDL, I was told that the small snack shop opposite AA 1st class check in will be turned into a McDonalds in the next few weeks.