I think the second scenario is a real rarity. I would say that it takes a very strong person to get out of the “college scene” and get back into yeshiva full-time. Since he stayed part-time, that might have been what kept it high on his priority list, but I think that most people, once they get involved in college, then they’re off to work because “what’s the point of having a degree if you’re not going to use it”. It takes a lot of yishuv hadaas to get back to kollel at that point. He deserves a lot of credit. I think it’s like people who I know who were in EY for a couple of years after getting married and decided they wanted to make a go of buying an apartment here and living here, but first went back to the States to work to make enough $ to have a nest egg when they got back. Most people would probably never make it back here after that, but I do know one couple that did. It wasn’t easy, but that was their goal together so they helped each other stay focused.
I also agree with the poster who said that it’s hard to imagine what kind of degree he had that it was so easy for him to get a job after he was in learning full-time for 10 years after getting the degree.