For background I have a 2g piercing and it is more than 3 years since I stretched it to that size so it is well healed.
I have one of the badassworkroom cages with the s hook for those of us with a foreskin. With the right kind of pliers you can adjust the positioning of the piercing. Every time I have done it I was worried about cracking something so I wouldn't recommend it, but it is possible.
I discovered that for it to be comfortable doing heavy yardwork the piercing hook needed to be 8mm further back than I had measured without the cage. That puts the piercing just barely inside of the actual cage.
Figuring out the correct measurements is a real challenge, but in general I would say that there are three points
The cage needs to be wide enough that it doesn't push down on the piercing when you are fully hard.
It needs to be long enough that it doesn't push on the piercing from the front when you are full hard.
The piercing need to be far enough back that it doesn't pull when you shrink.
I believe it is possible to meet all of those, but at the same time I have only been locked up for a week since the last set of adjustments.
If you have the time, determination and disposable income then a piercing is a serious option, but there are plenty of challenges.