Strength and hypertrophy question(s)

Let's say we have a guy trying to lose a crapton of fat who eventually wants to add muscle mass. It seems to be the consensus that his best path is to be at a caloric deficit to lose down to a reasonable BF percentage before starting to eat at a surplus.

During caloric deficit, he lifts as heavily as he can. He progresses in strength (or technique or whatever other factors are involved) such that he can lift substantially more than when he started. Use your own definition of "substantial," if necessary. Let's say he gains minimal, if any, muscle mass during the caloric deficit, but he's definitely stronger, at least judging by the weights he can lift.

At some point, he's ready to start adding muscle (knowing some fat will tag along) at a 250 calorie a day surplus or thereabouts.

Is this guy better positioned for hypertrophy during surplus than if he hadn't lifted during deficit? Presumably, he retained more muscle mass than if he hadn't lifted, maybe he starts off looking better, maybe even bigger, maybe not skinny-fat, so that's a benefit to having lifted. But, on day one of the caloric surplus, which guy is likely to have more hypertrophy -- either from an absolute or percentage perspective, if it makes a difference -- the stronger version who lifted or the weaker one who didn't? Why? Would the version who made less initial post-surplus gains catch up before the better version was near his generic/age potential and simply wasn't physically capable of more hypertrophy? Ignoring, for the sake of argument, the benefits of lifting while losing fat, how, or is, the lifter better positioned at the very start of the surplus phase? Would there be noticeable differences in progression between the two paths, anyway?