“I'm going to fail height-weight on purpose and get booted” – how would you handle this?

Close door counseling! I hate a punk!

Discharge for the good of the service.

Just get em out as fast as possible. You can waste all the time you want getting them the worst discharge possible to try and screw them but as my Sergeant Major wisely told me, "We don't bother trying to get a dishonorable because it takes longer and they're a cancer that is better off removed from the organization ASAP."

A good majority of people who apply to have their General discharges turned into General under Honerable or even Honerable succeed later anyway....so if you can't warrant a dishonorable discharge for something truly heinous...just cut bait and move on.

Give them what they want. Get the negitave out of the unit to keep morale up. It’s their life and to their dismay, bad conduct discharge, so git rid of the rif raf and move on.

Good Riddance. Who wants to serve with a soldier who does not want to be in thte Army. Moral and unit efficiency will suffer. Let him to ! There are others who want to serve and he can readily be replaced. Let him suffer the logical consequences of his action when he is a civilian. Dont care. Not the Armys problem and not my problem.

I believe that the reg states that after failing the tape test the second time, provided the CoC has jumped through their administrative hurdles, the CoC must INITIATE separation. Doesn't say you have to complete it.
I would inform Soldier of this loophole and also inform him that he WOULD be completing his enlistment, and that it was entirely up to him how smooth that term would be. This usually provides enough motivation for the kid to decide he will actually Soldier. Especially after the first few months of holding the line. And continuous counseling on motivation, both good and bad.
I am assuming that as a SPC the kid had already been in for a couple years and had 2 or less left to go. If he still had 3 or 4 years, the calculus may be different. At that point it may be better to cut bait, because if he doesn't shape up that is too long to carry dead weight... Plus it brings a large chance for him to PCS or to get in a new CDR who won't support that plan of action, which makes it just a waiting game for the SPC.

He's/she's dead weight. That individual has believe that they have some to contribute. If they're only purpose to is collect a paycheck, you don't need them. They need to find they're self worth and value first.

Encourage his success - in the civilian world.

As a leader, I have had good soldiers get low, even depressed over constant struggles with health related to PT and weight. The negative attention that singles out a soldier over these shortcoming, especially in today's youth often drive a feeling of hopelessness for success. While standards are standards it's important to ensure soldiers are counselled on not only thier shortcomings but their successes and positive contributions to the team.

Not just counseling in writing, but verbal praise and encouragement of thier value.

Showing proactive concern for why they have been on a profile for so long beyond and looking into thier "treatment plan" with your command weights value as well. I had a soldier transferred to me that over a 3 year period was on and off profile for the same ailment for all but 2 months of his enlistment. The root problem, new primary care that started over every time from the beginning. The soldier had given up. I took his history to our command. My commander made a phone call to the brigade Sergion on the soldiers behalf. In less than 60 days the soldier had a needed surgery and his motivation was ignited. He requested to stay on remedial PT through his post surgery physical Theropy and when he came off was in the 270 club. A 180 from the soldier that "just wanted out" 6 months before. Something others never thought possible

If I would have let him continue his path, he would have been out of the army, dealing with a life long lasting ailment induces by the service reeling in VA to fix him. Another broken statistic.

Fix him a big pan of Ex-lax brownies as a going away present and send him packing. If he's unwilling to fulfill his commitment to his country and to himself as a man, there should be no VA benefits awaiting him upon his return to civilian life.