If I reopened the case and tried to have the loans discharged, will the Trustee base their decision on my circumstances at the time of the bankruptcy?

Bankruptcy cases can be reopened. The trustee has nothing to do with determining whether a loan is discharged, the judge makes that decision. Usually, bankruptcy issues are decided based on the facts at the time you filed. There have been relatively few cases on the dischargeability of student loans based on hardship, so there is a chance at discharge. In order to have your student loans discharged, you usually have to exhaust all your other avenues to getting student loan relief. For example, if you have governmental student loans, have you attempted to get a pay-as-you-go plan? If private loans. Have you attempted to negotiate with the lenders? If not, you don't have much chance.

The Bankruptcy Judge, not the Trustee, makes the decision on whether or not a student loan debt is eligible to be discharged. You are welcome to reopen your case and file the appropriate pleadings to do this. May cost you additional fees to the court to bring an adversary proceeding to do this. The student loan company is likely to object to this application. The judge will base the decision on the evidence you present.

You need to engage a bankruptcy attorney, provide the details and procure an opinion.

In the 7th circuit (Illinois, Wisconsin and Indiana) you may reopen a case, but not if too much time has passed since the discharge. How long is too long? Probably a year or so. You would benefit from retaining a skilled bankruptcy lawyer. You will need to litigate the case, and experienced lawyers know how to do this better than laypeople.

You can reopen your case, but you have to file an adversary proceeding which is like a mini-trial and the chapter 7 trustee won't even be involved. Your bankruptcy judge will decide based on your arguments and the responses from your student loan creditors. If you have done some research, you should know that the "undue hardship" test for discharging your student loans requires that you demonstrate you will NEVER be able to pay them back. Your circumstances at the time you filed for chapter 7 are merely incidental. One of the things undermining many recent attempts to discharge student loans is the availability of income-based repayment programs, at least for federal loans. Judges frequently urge debtors to sign up for these 20 or 25-year programs at the end of which the remaining debt is forgiven. That is the timeframe you need to be thinking about in making your arguments.