The other thing that you have to decide is if you want to stay at Dyess or come to Ellsworth, my two cents, come to Ellsworth. On-base, from what I have seen is really nice, but I do believe that it is difficult to get on-base housing. It was when I was there, but things may have changed. I rented a house in Hampton Hills right out the main gate and it wasn't too bad. Other apartments to rent are Quail Hallow, not bad places either and close to work, . My advice would be to stay south of the train tracks down by the mall area or over by the zoo type areas. DO NOT rent from Gerard Real Estate!!! Completely ripped me off of a security deposit for stupid BS but wasnt really worth fighting them over.
The schoolhouse takes 6mo, give or take a couple of weeks or days, depending on maintenance and cnx'd sorties. Syllabus is 3mo academics and 3mo flying. PM me and I can give you more specifics on syllabus stuff