I just got back from my 4th trip THIS MONTH (Miami, Chicago 2x, Dallas), so perhaps I can give you some perspective.

First of all, checking bags is just a huge no-no, but you seem to have made your decision, so I can't change that.

I'd NEVER take any drug that would make me less likely to be able to function fully in the event of a plane evacuation, or, more realistically, to be a little unclear on directions about gate changes.

On most airlines, you're only allowed ONE carry-on and a "personal item" (like a purse). Even then, on my trip back from Miami, I was last on the plane (flying standby), and I had to check my carry-on, so that's why I wear a Scott e-Vest loaded with my toiletries, a book to read, various electronics (cell phone, ham radio), + spare batteries for electronic devices. When they force me to check my carry-on, I pull the laptop and tuck it into the seat-back pocke.

The worst thing about air travel is that it's almost NEVER ON TIME. I fly out of Newark and O'Hare a lot, the two worst airports in American for on-time departures.

Finally, be patient and kind to the people working in the airport - yes, even the TSA people. It's not a fun job.