I think that the window of opportunity is a very real thing. You do get used to the drugs and they do become less efficacious. Max out your weight loss while appetite control is high is as calid a strategy as any. Theres also evidence of the setpoint theory that your body will loose weight until it gets to its new “equilibrium”. In either case, the only thing that the take it slow approach can probably give you is more fat mass loss vs lean body mass if you train and eat properly.
Also regarding skin laxity i dont think there is any correlation. If your skin has stretched out beyond your elasticle capacity you will have loose skin. Period. Its genetic to some extent and depends on your fat gain %.