We always see the slowest boarding/offloading times when flying to/from Orlando, where the majority of flight passengers are either under the age of 10 or over the age of 70. The last time we flew it was to/from Edinburgh from Syracuse via JFK, and I could swear that it took half as long to board a 200-seat 757 full of adult tourists and business travelers at JFK as it did the 100-seat E190, full of disorganized families, that we'd taken from Syracuse.
LOL--DH and I have this technique down as well (although I don't describe his as burly...maybe more scrappy, but certainly strong enough to hoist those bag quickly and efficiently). When we have the kids with us, they follow in the center, leave their overhead bags and between our 5'11 DS and DH, they get those bags up and out of the aisle pronto! I slide into the seat nearest the window, flipping the armrests up as I go so that the kids can quickly scoot in and store our bags under the seats. Biggest pet peeve is the jerk in the row behind who feels he needs to push forward to get in front of us! Dude...pushing kids out of your way to save 30 seconds is NOT COOL!!
I'm glad you asked! I used to travel frequently for work, and after a couple of mishaps with my checked luggage, I committed to traveling carryon-only, and I've never looked back. Here's how we do it (to summarize, we bring only what we need, with a carefully-curated packing list that we stick to):
1 - Each member of the family has a rolling 21" carryon suitcase for his/her clothes and shoes. (The bags are the traditional style with two wheels, which have far more interior space than 4-wheeled rolling bags). For a trip to Disney World, those suitcases will hold (rolled carefully to reduce wrinkles, and placed into packing cubes) 5 or 6 warm-weather outfits (if our trip is going to be longer than 5-6 days, I simply bring half the clothes we need and schedule a relaxing morning doing laundry by a quiet pool, mid-trip), a swimsuit, PJs, underthings, and a pair of hiking sandals. An eBags pack-it-flat toiletry case with the whole family's toothbrushes, makeup and hair things, etc. also goes into the top of my bag. Because the kids' clothes are smaller, their carryons are only about 75% filled after their clothes are packed, so breakfast foodstuffs and miscellaneous items (a laundry bag, rain ponchos, glow sticks) get added to their bags. DH and I each slip our 3-1-1 bags (mine has cosmetics and toiletries, his is chock-full of sunscreen) into an outside pocket of our carryon, for easy access during security screening. Fully loaded, each carryon bag weighs about 20 pounds, so our kids (every since their first Disney trip at ages 4 and 6) have easily been able to pull their own bags.
2 - DH and I also each have a "personal item" for the plane -- a backpack for him and a tote bag for me, one with the strap on the back that allows me to slide it over the handle of my carryon when heading through the airport. My bag contains my park bag (a tiny crossbody purse with my ID, cash, travel documents, phone, 3x5 itinerary cards with confirmation #s, our MagicBands, etc.), a mini First-Aid kit with Band-aids and Tylenol, wet wipes, sunglasses for me and my daughter, my camera and any other electronics, earbuds and chargers (packed into a clear pouch for easy inspection during security screening), and any in-flight snacks for the family. DH's backpack contains his ID/cash, sunglasses for him and my son, his own electronics and accessories, and any extra items the kids may want in-flight. For our first trip, we also had the kids bring backpacks as their personal items, but we found that they just got in the way, and the children only had a book or two, and a pair of earbuds that they wanted during the flight, so we just consolidated them into our own personal items on future trips.
3 - We wear our bulkiest clothing on the plane: long pants, sneakers, a short-sleeved top, a hoodie, and for my husband and the kids, a ballcap. This saves space in the luggage, and is generally appropriate for the weather at home anyway. We usually travel to WDW in fall or spring, and most times we never had to break out the hoodies or jeans again until the flight home, but they're nice to have in case there's a cold snap. If we think we'll want to change into shorts in-flight or as soon as we get to Orlando, we keep an extra pair of shorts in my husband's backpack.
Easy-peasy!
You're right -- when DH and I flew recently, they had to make that announcement for each leg of our flight. It was also very clear that a lot of people were deliberately bringing oversized bags to the gate that they knew wouldn't fit into the overhead, and then waiting for the "overhead bins will be full - so we'll let you courtesy gate check now if you like" announcement to bring them up and get them gate-checked for free, in order to avoid paying a fee to check them in the first place. It's a "hack" I've actually seen recommended on some frequent traveler websites. We most often fly JetBlue, which recently went from giving everybody one free checked bag, to charging for it, so suddenly the use of this tactic has skyrocketed.
I also wish that flight attendants would take a more active role in instructing people who do bring a carryon in where to put it (e.g., somewhere in the vicinity of your own seat, wherever possible). It drives me nuts when I see somebody waltz on with a boarding pass for the last row, stuff their bag over Row 1, and then amble back to their seat with their nose in the air (meaning, some poor soul from Row 1 is probably going to end up having to go back near the end of the aircraft to stow their bag now, delaying boarding, and then will have to fight their way back like a salmon upstream to get their bag at the end of the flight, delaying the disembarkation process). I try to be like a "travel ninja" -- so fast, efficient and unobtrusive that no one will ever have cause to feel I've delayed their forward progress for a moment. DH and I have our whole boarding routine down -- I go first with my carryon behind me and he follows with his in front. Once we reach our row, I let go of my carryon and grab DH's personal item (backpack), and DH, a strong, burly fellow, hoists both of the carryons (which are 21" and lightly packed, about 20lbs. apiece) into the overhead while I slide into the window seat and stow our personal items. We're both seated with seatbelts buckled, high-fiving like the dorks we are, within 5 seconds of reaching our row (10 seconds with our two children, who enjoy making a game of who can get settled more quickly). Then we spend the rest of the boarding process people-watching the non-ninjas and quietly judging them.
). I need to see if I can still set up the interview or if we need to submit the application fees all over again. Totally no excuse for forgetting other than I have mom-brain 
