They have been far removed from real life for most of their life. Yes they spent time pioneering and paying their own way, but I would bet most of them received assistance from someone who was working full time. Eventually, though, they became employees of the org and had all of their expenses cared for and received plenty of supplements from others. I've heard the story so many times from those that were in Bethel or who served as missionaries or special pioneers that they received gifts (at just the right time of course) or cash or plane tickets. There is no way this organization could continue if everyone followed in their example, found part-time work, and pioneered. There would not be enough money coming in to run Bethel or support the missionaries.
The guilt is just another way to trap people and coerce them into doing what they want. Funny how JWs readily spout how Jesus taught that the Law put on people and his load is light, but don't see how the organization, specifically the GB, have returned to adding on a heavy load.