We are neither digitigrade nor plantigrade exclusive because as hunter gathers, we have evolved to take advantage of both which is more selectively fit than one or the other. Our feet are designed to flatten out when we need to cover long distances, but when we are ready to stalk, fight, and chase, we go up on our toes just like digitigrade mammals.
If a person were digitigrade exclusive, then he would not be able to keep up with the migration distances of hunter gatherer societies. He would develop neuromas or other foot problems at an early age causing foot pains that would make him vulnerable to predation or death in battle; so, to answer your question, people are more likely to evolve digitigrade exclusive feet now that it is no longer selected against than he would have as a hunter gatherer.
Mammals that evolved to be digitigrade did so not because they were hunter gatherers but because they were quadrupeds. Quadrupeds can distribute their weight over more appendages; so, specializing makes more since for them.