We pay for everything. Hell, we pay her car insurance, her phone, blah blah. Just feel we are making the same finance mistake. It's tough. You show them care and cross your fingers. Ha ha
Luckily for me my daughter is a lot like her mom. Always looking for bargains and doesn't spend what she doesn't have. Always been good with money even though we have done that same as you (pay for everything which I am not a fan of). I am not sure how my son will be when it comes to that. He understands not to spend what he doesn't have but he hasn't been paying for things either.
Both my kids played sports through high school and got very good grades. Because of that they were always busy and on the go so we never really made them get jobs. Even now (son in college) my son is playing college baseball so it makes it really tough for him to get a job and stay up with baseball and school. He is doing well in each of those (all A's his freshman year of college and has gone from a walk on to earning athletic scholarship money as well as academic scholarship money) so it's hard to force him into a job when he really doesn't have time and has kind of "earned" money for school with his scholarships.
Both had credit cards that we paid and they were allowed to use for specific things (gas, food that we would have paid for if there, clothes - is asked first). Things that we would pay for as parents if we were with them. Extra stuff they had to use their own money (from b-days, graduation, side jobs, etc). I think they have an idea on how to not overspend.
I feel for your situation with a kid in debt. My daughter's husband has had a hard life and made some bad decisions (two failed marriages under the age of 30). Because of that he has debt but not due to frivolous spending. She decided to marry into this (would not have been my choice but she is an adult and made her choice). Legal fees (for custody etc) has put them in a hole. We have loaned them money to cut down on interest and getting in bigger holes and I wasn't a fan of doing this but my wife pushed for it. They are making their payments and doing mostly the right things but there are still some things that irk me. Very tough situation for me at times.
Overall I am proud of both of them for the kind of people they have become. I just don't agree with all their choices hahaha. Gotta let them live and learn at some point and just hope the lessons they learn aren't too damaging to recover from.
There is no right answer to these things. Just do the best you can and hope things stick. Eventually they are adults and have to make their own decisions and live with the consequences.