You could try is connecting with a lawyer through the Massachusetts Bar Association's "Dial-a-Lawyer" program. It's only offered on the first Wednesday of every month between 5:30 and 7:30 pm (call 617-338-0610). You might not s;peak with a bankruptcy / tax expert on that call, but the attorney on the phone should have access to a listing of other potential resources for you beyond whatever help can be offered at that time.
You could also reach out to the Volunteer Lawyers Project in Boston (http://www.vlpnet.org or 617- 603-1700). The scope of matters they handle tends to be a bit broader than many other legal aid organizations (in your situation, for example, I believe they have attorneys who can help with bankruptcy issues). Again, if they can't help directly, perhaps they can put you in touch with another potential source.
It is difficult to answer about the best approach to the IRS or whether to file for Bankruptcy without more information. However, if you are seeking to locate pro bono or low cost attorneys, you may try some of the links below. The first is Greater Boston Legal Services. They offer services based upon income to 31 cities. However, your tag indicates you are currently in Lexington and GBLS offers services only to Lexington residents who are over the age of 60. They are a good place to start and perhaps may know of additional resources for you. The other two services are lawyer referral services. Specify your situation when you call and they may be able to direct you properly.
Greater Boston Legal Services
Boston Bar Association Lawyer Referral Services
Massachusetts Bar Association Lawyer Referral Service
My responses here are do not create an attorney-client relationship. My response is based upon the very limited details of the submitter and should not be regarded as legal advice. I am licensed to practice law only in Massachusetts and any information given is limited legal opinions based upon Massachusetts Law.
You can also try your local Legal Aid office since it sounds like you'd be eligible, although I doubt they handle cases like this with the IRS.
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