So I'm the guy that gets on the plane before everyone else. I fly a lot, in the front of the bus. 100k miles a year. So while not a direct answer here's my seasoned traveler advice.
If travel is a common thing I'd invest in an airline card. Instant status, and you get free checked bags. Call and get the fee waived. Usually you'll get bonus miles, so one or two trips will get you a free round trip.
If you travel overseas get global entry. 100 bucks gets you kiosk entry an no lines. It also gets you precheck. I go thru the security line on average 2 minutes. No shoes off, no laptop out, no toiletry bag out.
Re-read the regs often as they change all the time. Small knives without locking blades under 2.36" are permitted. Generally tools under 4 inches are. I bring fly tying stuff.
By the way I've never slept in an airport or waited in a line after a cancelled flight. But that's a different story.
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