let us know how it went. To me like anything related to airlines, who the fuck knows..... I've had no problems with connecting flights before, does that mean it'll never happen? The best info I heard recently was Nora explaining how she just checks her board now because she's run into too many problems.
Generally speaking, I'd say you're good 90% of the time. Some of my general rules of thumb are:
1. Take the trucks/wheels off and put them in your bag. Then conceal the deck in something if you can - I put mine in an ikea laundry bag, roll it up, and carry it by the handles.
2. A budget airline is much more strict on luggage limits and weight. If I'm flying a budget airline, I always hide the deck behind my backpack. You only really need to do this at the check in counter (if you need to go to it) and when boarding.
3. I try to not take a brand new deck. If you have to straight up throw it out or check it, 100% sunken costs. Almost always cheaper to buy a new one at the destination vs the check a bag fee.
This year, during a transfer in Rome, I almost had to throw the deck out. Some security person grabbed it and said they weren't allowed in flight. She went to check with someone and eventually they let me take it.
Even more recently I had a flight out of Istanbul and they said Turkey actually had some official aviation rule that stated skateboard decks weren't allowed in flight. This was also during security, which was after passport control. They said the only way to get it back was to have someone from the airline come get it with me and check it. I got lucky in that I wasn't flying a budget airline here so they were cool and got it for me.
Also, in New Delhi, India they only made me check the trucks. In Vilnius, Lithuania they made me throw a skate tool out.
That's all just to say, you're mostly good but never know - especially with international flights. I do think in the US taking a skateboard on planes is a bit more chill than in other countries.