From what I understand, Japan during World War 2 established significant garrisons on dozens of islands assuming America would shed significant amounts of blood and resources taking each island, whittling down America's forces for a final decisive battle.
However, nearly all the islands lacked sufficient local food sources for the size of their garrisons. They also lacked industrial facilities and oil wells thus they were reliant on shipped supplies to remain combat effective. Did the Japanese high command not take into account that their supply lines would be disrupted or that America would just ignore or isolate Japanese occupied islands?
Your question is putting the cart before the horse somewhat. If you rewind to before the war begins, things make more sense.
The Japanese plan embraced an abstract concept of attritional warfare, in which the defense network as a whole would consume so much in the way of American resources should it be attacked that it was assumed that the US would lack the will to engage in a costly struggle over unknown jungle fortresses of no relevance to the American voter, especially if the American Pacific Fleet was crippled first. This was the first of several errors of judgement, since they viewed the strike from a purely military and Japanese cultural perspective. They did not understand that the surprise attack would so offend the American sense of fair play and “proper” war that, instead of causing the US to think of how terrible a position they started the war in, it caused them to be inspired to fight it in a way a more traditional declaration of war would not have. The hoped-for impetus driving a morale-draining attritional struggle was thus lost at the outset, as it was no longer going to be an impersonal battle. In short, the Americans started the war willing to bleed.
In terms of supplying island garrisons, another major error of judgement was that the Japanese greatly undervalued marine logistics. This is why their merchant marine was so vulnerable to destruction by American submarines. Too, they faced constant material shortages and a general low industrial output, so almost everything was difficult to replace. This meant that once they began losing supply ships, they had a great deal of trouble replacing them.
More importantly, though, armed forces tend not to plan for defeat, and the Japanese were no different in that regard. You can’t just take and hold only those areas that have everything you need to supply a modern military garrison all by themselves, because there’s very few such places; in the Pacific island chains where all these bases were built there’s none. As such, every garrison is innately going to be dependent on outside supply, which in turn relies on your navy and air force continuing to be in control. There's little point drafting an initial strategy for a war you plan to launch that presupposes a complete loss of air and naval dominance (not to mention that even if they wanted to, it was of course literally impossible to just make an island have the oil required, or the agricultural area and workers needed to feed everyone at every base).
To sum up, talking about how the Americans might choose to bypass certain islands and move to other ones presupposes a freedom of movement on their part that in turn is predicated on their having offensive superiority and the will to use it. The Japanese planned to start the war, and to win the war at sea, and this shaped everything they did. You don’t have to worry about the supplies to your island garrisons being cut off if the American fleet is at the bottom of the Pacific and your ambassadors are dictating the peace, which is generally how they assumed things would end up.