At some point it boils down to desire. Here's a real life example of two skiers in recent years introduced to skiing by our core group of skiers. They are both financially capable of going "all in" so that part is out of the equation.
Skier A obviously enjoys his time on the water with us and has improved drastically. Has only come out a few times each year, although the offer is pretty much standing anytime he wants to join.
Skier B has now completely changed his lifestyle and purchased a new slalom ski, gloves, life jacket, trick ski, Malibu TXi, and a house on the river approaching 500K. Breaks ground on a new boathouse for the TXi very soon.
Skiing is not for everyone, and if someone really wants it they'll find a way to make it happen.