We always make sure everything is in a bag too... this year I had the brilliant idea to not only put everything on a bag, but make sure the bag was easy to carry. I clipped a "mommy hook" onto the bag and clipped multiple bags together so there was just one action of taking things out. (each kid got a little toy in a disney bag) When we got out of the tram, we just clipped the mommy hook onto the handle bar until we got through bag check, then restuffed everything into the stroller.
This August they did check our stroller baskets for the first time, but it was every day for 2 weeks.
For the tram, if nobody is using the handicapped seats that was the only door that we could actually get the stroller into without the second person's help. DH and I usually each held one of our sons- I could lift the stroller up myself and it fit between the seats in that row only.
The other rows I needed somebody to help lift the stroller and then it didn't fit on the floor between seats so it had to sort of balance on the edge of the seat and took up it's own spot. One tram driver yelled at me to fold up the stroller before realizing that it was folded it just wasn't fitting.
The biggest tip is to ignore if anybody glares at you, they are likely just having a bad morning and haven't paused to think about the fact that you are struggling with the stroller and doing your best. They will get over it once you and your kids are safely loaded.