OP - personally I'm amazed and a bit appalled that you're complaining after getting $250 in e-certs when it seems that the 1) you got a bonus upgrading all with e-500s to begin with and 2) the gate agent was following the rules. IMO, you deserved nothing at all for these indicdents other than a redeposit of the two certs they took from your account when the system overcharged you. Of course politely asking for a supervisor at that time instead of creating a hostile environment with the agent wouldve served you better to address the issue, as well.

- You can only upgrade ONE passenger travelling with you using 500s regardless of your relationship or anything else - ONE - you were allowed two which if someone else was waiting for an upgrade that you got, its unfortunate for them as the rules were bent for you regardless of what a telephone agent had told you. That is not an easy route to upgrade on depending on day/time of travel so be very happy you cleared at all, esp under the circumstances.

- There is no pre-boarding of families on UA - period. You have no idea what the deal was with the other parent and stroller in front of you. 6A is a bulkhead so maybe she was with someone in a wheelchair that was just taken down or a crew member or gs, etc ... YOU have no clue so for you to go on a rampage is well,