I will be using paper maps. Due to my low experience in taildraggers, I worry about landing at airports above my crosswind capability and for the most part have identified alternate airports with different runway directions to get better crosswind components. However, I would need to know the wind direction in flight to decide which airport to land at.
So legality aside, will the cellular data or cellphone service work on an iPad or iPhone in flight for flight safety purposes?
You only need to look at your 496 WEATHER info if your airport is on The System
And if your airport isn't in "the system", it won't show up via any cellular data on your iPad. The only case where that might be different is if there's an ASOS/AWOS that can be reached by phone but isn't reporting in the system, and I don't know if there are any such airports.