Both the Revolutionary War and Rip's wife represent the pressure of personal responsibility. Rip prefers to avoid all labor and responsibility, and in fact is allowed to escape his obligations through his magical sleep. The War, in which he would have been expected to fight, ended with victory at the cost of many of Rip's friends. His wife, who wanted him to work harder to support her and his household, died without ever knowing what happened to him, but generally in high spirits, as she was described as taking joy in argument. For Rip, with both of those major headaches out of the way, he found himself free to enjoy his old age:
Whenever her name was mentioned, however, he shook his head, shrugged his shoulders, and cast up his eyes; which might pass either for an expression of resignation to his fate, or joy at his deliverance.
(Irving, "Rip Van Winkle," bartlby.com)
This shows how his sloth was indirectly rewarded; Rip now can live in ease and without the worries of personal responsibility, as he is old and the working world is a young man's game. Instead of learning a lesson -- for example, the loss of experiencing his children's growth -- Rip has had his initial philosophies confirmed. Both the War that he skipped and the wife that he skipped out on were things that should have enabled him to grow as a responsible adult; instead, he moved from irresponsible youth to irresponsible old-age without any real problems.