$50 a year, or whatever you want, seems so fair for lunch money. The envelope system has worked great for me. I have bought six years of YNAB now. I haven't been perfect with my finances in that time, but using a legit budgeting software makes tracking and planning your spending so doable.
I think I would be in a legitimately worse spot without YNAB and ultimately probably would have never ended up here. I used Dave Ramsey's every dollar back in the day. It was a good starting point, but ultimately I liked YNAB more, mostly for the envelope system.