As weekends are generally less in my control, I'm going to aim to post on weekdays only.
That said, since stuff came up yesterday and I'm at home now, I'll do a quick catchup.
The loan payment went through yesterday, the 17th, and they listed it as having been posted on the 15th, so looks like the student loan payment issues have worked themselves out.
I am also currently leaning towards paying off everything but the large subsidized student loan before going back to school. That's about 14500 in principal to pay off, clearly a not insubstantial amount, but less than the 38000 that will be remaining. That will mean when I'm done there will (hopefully) just be one loan to pay off. It also means with the payments I'm making now it will get rid of about 25% of the debt, but 30% of the monthly payments. I'm still not sure paying any of it off makes the most sense economically, but emotionally it will be nice to start whittling it down.