I have flown probably 20 times in the last few years with a board. Small breakdown of the things I have done
-Back pack as carry on, fully assembled board as personal item. Back pack under seat, board in the over head.
-Flying southwest I have checked the board as my second free bag, just stuck the luggage sticker around the deck.
-Trucks and wheels in back pack, brand new deck in wrap strapped to backpack.
-Strap complete to back pack and waited for the "we're looking for volunteers to check carry on" then checked my carry on luggage bag at the gate for free and did step 1. Used this one for a shorter weekend trip.
The only time I was ever given an issue was sitting in an aisle seat with a board under the seat in front the flight attendant said it was a trip hazard in case of emergency and tossed it in the over head. The beauty of the skateboard being thin is you can still fit it on top of bags in a full over head bin.
I have never had any issue with TSA, when going through security I do unstrap it from the bag and send it through xray alone. FWIW I also have TSA PreCheck and those TSA employees are usually more chill, except for Oakland, that airport is absolutely the worst.
Gearing up to go back to England next week and taking a board for sure.