my suggestion, before someone financialy committs to attending a school-is to see what the realistic marketability of the degree/certification they are looking at is.
we live in an area with lots of higher education opportunities-high prestige private universities as well as public universities and community colleges well thought of, and mass marketed trade schools.
the universities that are realy invested in their students, have, in the last 2 years, drasticly cut back on certain programs. they look to the employment statistics for their grads. and in some cases have reccognized that there is absolutly no job market for them. because of this they are not accepting admissions into those programs until further notice. other colleges and trade schools that are more concerned with simply collecting tuition and graduating students are continuing the same programs and graduating hoards of students that will find themselves no more employable than prior to when they enrolled, and saddled with student loans to boot.
college is SO different than when i went in the 80's and when dh got his degree in 2000. beyond the much greater cost, it seems like the course requirements entail so much more outside work (even if you are doning one of those designed for working adults)-it's a TREMENDOUS time committment.
realy review tuition assistance programs with jobs, often times unless the classes will benefit the current employer there is no financial assistance, and be cautious taking summer courses through certain colleges and universities-at our local university the summer courses are 50% more expenseive than the identical courses offered during the traditional school year because they are taking advantage of employed professionals looking to take c.e. courses during the summer months.
He is an extremely intelligent man who got by with no degree all these years making a very good living. Then, this economy hit and he was unemployed and no one would look at his resume without the degree, no matter what his experience was. He did find a job and will be promoted Jan. 1st, but now he's determined!
It looks like if he does the letters, arts and sciences one he should be able to do something at the same company he's been with now for 10 years. It also looks like the easiest course load (they have examples on back) it would be for 4 semesters no going for summers. 
We are also open to moving for a higher paying job or him driving a little bit more.. he only drives 15 min to his job now.. plus he says he likes a little drive after work to "relax" he use to drive over an hour
