Rip's "meekness of spirit" means that he is most definitely not a leader, alpha male. His character type is hardly ever seen in modern media examples. Hyper-masculinity is the name of the game in many of today's movies, TV shows, and video games. Rip Van Winkle is the antithesis of that character archetype. In fact, Dame Van Winkle is that archetype. Rip is described as having a meek spirit, which is then expanded upon. He is said to be kind, patient, helpful, and honest. About the only negative that the narrator mentions about Rip is that he avoids doing his own work at all costs.
In a word, Rip was ready to attend to anybody’s business but his own; but as to doing family duty, and keeping his farm in order, he found it impossible.
The characteristics above grant Rip a great deal of popularity, because those are all characteristics of a good friend. People like to be around Rip, because he's not pushy and overbearing. His wife is, and the people know this. That knowledge grants Rip a bit of extra sympathy from people as well.
Certain it is, that he was a great favorite among all the good wives of the village, who, as usual with the amiable sex, took his part in all family squabbles; and never failed, whenever they talked those matters over in their evening gossipings, to lay all the blame on Dame Van Winkle.
Simply put, Rip is popular because he is so pliable and easy going. He's the friend that does whatever you want to do. He won't ever push his own will and desires on a situation. I've had friends like this. I never considered them weak or stupid, and I always loved hanging out with them, because they always just went with the flow.