His first time at 4CC?
I'd imagine the best stratergy would be to follow a strategy that they themselves came up with: trying it out at lo-lev summer comps.
The problem is he can land all the quads he wants in summer comps (which is best for me on a selfish level) but he still will have to land his first in an ISU competition.
Even a senior B/Challenger skate, there will still be pressure to land his first on the grand prix (with an implied or better tacked on the end).
I would not be surprised if we see it in an exhibition first, but we would still have to see it at a major competition.
He appears to be a late season skater, so i am not sure the grand prix is a great time to try his first quad. He did his first 3A at the JGPF, so that could be a good time, but at the same time, much risk right before nationals. I don't think he would put his first quad in at the GPF right before he is about to defend his national title for the first time, likewise I don't think we will see it for the first time at nationals next year with him trying to defend.
As for next year, I suspect we will see him at Nebelhorn again so he can learn to defend, but I don't think a first quad is going to come when he is learning to defend. He likely will get Skate America again, and with Machida out, he is in a very similar learning to defend role as likely will be the highest ranked returning skater. Under Miss Universe rules, he would sorta be the defending champion as the winner did not complete their reign. So I don't think we would see a first one there. So that leaves one grand prix next season we could see it. . . meh.
Four continents is not that big in the USA, at least compared to Europeans. His doing poorly there with a potential botched quad attempt would be less noticeable, or upsetting to the powers that be. Also, with 4Cs countries always get 3 spots, so there are no spots on the line. Frankly that is why Adam is there, he can try as many quad lutzs as he wants and it will not matter if he comes in last, we still have 3 spots next year. So there is not a lot of risk to trying stuff at 4Cs. You are not playing with spots for your country, so that makes it in my eyes a good time to experiment.
If he tries a quad there, he either send the clear message that there is a reason he does not, so lay off and appreciate a well done quadless program of redemption at worlds. Or he lands it and may actually manage a win. No one loses spots, no one else is hurt, the USA does not seem to suffer reputationally, and then he is set up knowing what he needs to know for worlds. Heck, even next year 4Cs could be a good first attempt option after low level summer comps.