Delta and American went swimmingly. Trusted the wording on the policy.
On Southwest right now and their policy is worded a little more funky:
“Skateboard (manual or non-electric), may be substituted for a carryon or a checked bag. If the skateboard fits under the seat, it does not need to be in a bag or covered, but it does have to be stowed with the wheels up so that it doesn't roll. If stowed in an overhead bin, a skateboard must be stowed with the wheels up and needs to be in a bag or have the wheels covered (trash bag is acceptable) so as not to damage other articles.”
Did trucks, wheels and tool in a plastic grocery bag in carry on, deck separate. No problems getting on, flight attendant was super appreciative, probably how I’m gonna do it when I’ve got the time moving forward