You are obviously on top of it now and have a plan. A couple of things I might add to the conversation (may have already been posted, I did skim a bit).
You mentioned you’d never bankrolled him before and he’s had a job since sophomore year in HS. I might suggest that these are not new spending habits but that you didn’t have visibility to them before since he was bankrolling himself. The junk food, the uber rides, it adds up FAST and add in travel on top of it and it spirals.
My S17 has worked since junior year and has saved little to none, bankrolling the same type of activities. All social outings, not drugs or mob or whatever. And yes, treating others. His money, his choice. But my money is a different story.
I did not give him a CC as I didn’t want him to be tempted. I suspect the no remorse may be resentment about not being able to bankroll himself and if (like I am) he’s been told no job freshman year or first semester this may be a passive aggressive way to maintain what he perceives as a needed lifestyle. If he is known as the bank, he may be reluctant to give that spot up if it aids him socially.
What I’ve done, and may or may not work for you is that I have access to both his debit and savings and his spending money is in the form of a weekly allowance. He’s not capable of budgeting unless he really really wants to save for a specific thing and will spend in the spur of the moment. Rationing the funds helps him stay on track. He knows this.
He has made some poor spending choices over these first few months and has been “broke” and unable to attend certain things or buy food, and has been called out for being cheap by some at his OOS school. My position is while that’s unfortunate, it is how he will ultimately (hopefully) learn how to budget. He is acclimating. And plans to work 2nd semester lol.
The spending, in and of itself, does NOT mean, in my book, that there is necessarily an academic issue. What are the grades like? Can you see? I might make that a requirement for continued funding if you cannot. It’s a requirement for me, not because I am worried per say but as the person paying the big bill, I want to keep tabs just in case. He knows and that helps. Then again, his scholarship gpa requirement helps as well.
I’d be more concerned about the trips to Eugene, that’s not establishing his own life. Once a month? Maybe. I get missing friends but every weekend is too much and it was too easy to do. Forcing him to connect locally is a good thing in every way. The good news is if he is known as the bank at U of O, it may be less of an issue at OSU (socially) for him to change that dynamic.