Is there a reason you file so early?
The average person files later because we need time to get all of our documents (W2s, 1099s, etc). I pretty much file before everyone else I know, and that's in February (my financial institutions get their forms to me quickly, my workplace gets me my W2 the day after payday, and I have a pretty simple tax return).
The only document you'll need to worry about for your student loan will likely be your 1098-E, which is for your student loan interest deduction.
Even when I defaulted, I received one, so as long as you qualify you'll get it. Once you are no longer in default, it might be easier to get it from your servicer (mine was available for download pretty quickly).
Okay, so what I've gathered so far:
1. File taxes after my 9th payment (February 2020) and I have until April to do it.
2. Keep track and documentation of everything from start to finish.
3. Keep tabs on when I who my new servicer is.
4. Once I'm no longer defaulted, ask for a 1098-E from my servicer.
I usually file my taxes around the first week of January. My question is, if I file my taxes in say March, when does the count on my income stop? It just stops on my last pay of December? (I'm asking because if I make "too much" my medical insurance will go up and that's more expenses I have to think about). That's also another issue with filing early, I have until December 2019 to renew my medical insurance, what would I be putting as my income if I were to file in March? I think I'm going to speak to my insurance about this one, I'm sure I'll figure it out.
I used the repayment calculator, if I make the same amount (with a 5 % interest) the options for "Standard" is $257 / mo. for 120 months for a total of $30,889. My current "balance" is $ 24,248, even though bills in the mail say its $28,000 (about that amount). For what I earn $257 eats a lot out of my pay, I pay something like $300-$350 in bills and my job is not steady so I could be working 86 hours two weeks and 70 hours the next two weeks. Sometimes I'm working only 40 or 60 hours in two weeks total. I'm currently in the process of leaving my current job (doing a part time job) and just saving up for next year to still be able to make payments.
I have a question though, if I have "9" accounts and I'm paying say $257 a month, is the $257 being put towards all 9 accounts? Wouldn't it be better to consolidate them into one loan? Or is that too much for a loan of $20,000+? When should I consider consolidating or can I even do that if the amount gets smaller?
I also ordered out all my loans (not including the full account numbers) to get a better idea of where I'm at: