Always good to share positive experiences (there are so many negatives).
I've made it a habit to ask the ticket agent when I check my bag as well as the gate agent. You'd be surprised how many times the TA will tell me one thing and the GA will tell me the opposite. Maybe the TA has it wrong, or maybe the time through security, train, and walking the concourse is enough time for things to change....?
If I can get a bump and more miles/Delta$...works for me. At some point, I'll need it. I may be going overseas. If I'm not allowed to book directly into Business for it, I'll pay for the upgrade myself via Delta$... which will score me more miles/MQMs - a lot when considering an overseas flight and I normally fly domestic.