For what it's worth, Phil is my fiance and I've always felt he should go back to school. It's the timing (read, finances) that have been the on-going issue for us. He always was going to be a teacher, probably special ed, but from what I understand from him, he tested fine on the state's test, but was still not let into our school's program because their academic standards are much higher than the state's. I know Phil had some trouble grade-wise when I first met him, but now that he has a degree, his GPA has gone up since that time. From what he's said, I think it would be another year of class to finish the credits for the ed degree, and then the semester student teaching (I think our ed majors who finish the program straight through are in college for 4.5-5 years). However, if we moved to another state, he might have to start over because the ed credits he had before he wasn't in the program would not transfer.
Anyway, I really really think he needs this degree because 1) it's what he's always wanted 2) it will give him a larger range of job options when combined with his youth recreation degree and 3) it will give him more stable and widely available job options.
The problem right now is this: together we owe over $100,000 in student debt. My parents haven't helped me financially since I was 17 and pretty much the same for him. So, we have the debt, are still working on living arrangements, and neither of us have found jobs despite each of us applying for like three jobs a day. West Michigan is one of the worse places in the country to find jobs right now. Our local economy has lagged behind the rest of the country for years now and it's not getting better. I really have no clue how we are going to afford rent, paying debts, paying insurance, paying for Phil's medication, and somehow putting him back in school full time, even if he went to a crappier school.
Longterm, I think this would be wonderful since we are still researching opportunities for Africa and if this doesn't fit there, at least he will have a career to come back to (and as an enthusiastic male special ed teacher, he'd be almost guaranteed to find a job easily).
Edit: I'm an ISTJ, btw