I was very used to sailing with a tiller, having learned to sail on dinghies. My 28' boat also has a tiller. It wasn't easy for me at first to steer with a wheel, but now I transition back and forth easily. I still love the feel with a tiller - there's a more direct connection to how much pressure there is on the rudder. On bigger boats, though, that pressure can become a problem! Learning to steer with a tiller is probably more difficult, but it teaches you more, too, about the physics of sailing. A wheel is deceptively easy and familiar to use, but is really nothing like steering a car.
I was very used to sailing with a tiller, having learned to sail on dinghies. My 28' boat also has a tiller. It wasn't easy for me at first to steer with a wheel, but now I transition back and forth easily. I still love the feel with a tiller - there's a more direct connection to how much pressure there is on the rudder. On bigger boats, though, that pressure can become a problem! Learning to steer with a tiller is probably more difficult, but it teaches you more, too, about the physics of sailing. A wheel is deceptively easy and familiar to use, but is really nothing like steering a car.