I'm like 6-7 so far this year, with the one exception being a self-inflicted red-eye between Seattle and Chicago and two job interviews, basically staying awake 32hrs and having to change out of and back into my suit in those United Clubs. Other than that, it's been smooth sailing. Get an Airbnb app, an Uber app, and the United app. You'll never again have to pay for parking or wifi where you live; you'll never again have to wait longer than 5-10min to hail a cab; and you'll never have to wait in assinine lines just to print out a boarding pass. Traveling is not too hard when it comes down to it. The only thing you cannot control is weather, but it sounds like you use American a lot which is your bad. Don't blame the weather on having to use *****ty connections thru Dallas.
I try to avoid flying and I'm now driving to nearby cities. Some weekends, I rather stay in my ****ty city than fly. The problem starts with not having a direct flight from Philly to Austin. Some people might disagree, but I'd rather not get status when there's another airline with a non-stop direct. The apps above are good. Hotel Tonight or Priceline if you aren't building up rewards points. Having unlimited wifi or a paid hotspot is good too. Hope the paycheck's worth it, but at least you get points?
On our trip to Vegas last week, we made it through security and to our gate in less than 20 minutes. Had our bags and rent car 30 minutes after wheels down. On the way back, we took a shuttle from Venetian to airport and we were at our gate 22 minutes after we loaded onto the shuttle. After we landed at Hobby, we had our bags and were exiting off-site parking garage in 20 minutes. Sorry!
My wife's flight from Tyler to DFW was delayed so she missed her DFW-MSP flight and had to take the later one. However, her bags made the flight she missed so they were waiting when she arrived at MSP. When flying home from Italy a few weeks ago, I fortunately read my email around midnight the night before we were flying home and found out they moved our flight UP an hour. We were scheduled to fly from Florence to Amsterdam at 12:45 PM and instead were rescheduled to leave at 11:45 AM. Turns out it was due to an Italian ATC strike that was to occur between 12:30 PM and 4:30 PM. We were the last plane out of Florence until 4:30+ PM.