I also think you need to check with your attorney to see if he/she can find any obscure legal provision that would allow you to correct your earnings record with these tax returns (because you did pay estimated taxes) and if the lawyers' office doesn't understand your question, it is time to find a new lawyer. If you can succeed at that, it will push your date last insured to a more recent or future date so your current medical condition and current medical evidence will then be material. Right now, all SSA can use is the medical evidence before your date last insured, 12/31/12.

About your question about medicated or not. Many people have conditions that are kept under control with medication. If the condition can be controlled with medication without side effects that are severely limiting, then SSA will probably not find you disabled.

Again, your attorney should be answering these questions now rather than waiting until the hours before a hearing. You might decide that you will continue to take the medication that allows you to work and keep working (and filing timely tax returns) and wait until your condition becomes worse before filing.

Also, since you mentioned your 1099's from stock sales, I will make the assumption that you would not qualify for the low income SSI program because of the value of your assets. So with DLI in the past and excess resources for SSI, you won't qualify for anything, regardless of how ill or disabled you are.