I would be less-concerned with the mechanics of paying these bills, and more concerned with how to do this and remain within the legal boundaries of a 501(c)(3) nonprofit. You need to consult with an attorney who represents nonprofit entities. Also, the individuals receiving assistance can place the nonprofit's name in their HIPPAA disclosures as authorized to receive medical information - I think it is necessary to even see their billing statements.

*Due to the limitations of the LawGuru Forums, The Gibbs Law Firm, APC's (the "Firm") participation in responding to questions posted herein does not constitute legal advice, nor legal representation of the person or entity posting a question. No Attorney/Client relationship is or shall be construed to be created hereby. Further, information you provide to the Firm through this website is not confidential - it is available publicly to anyone visiting this website. The Firm shall have no obligation to keep the information you provide herein confidential in any context. The information provided herein by the Firm is general, and requires that the poster obtain specific legal advice from an attorney. The poster shall not rely upon the information provided herein as legal advice nor as the basis for making any decisions of legal consequence. As required by 11 U.S.C. §528, we must now disclose that, "We are a debt relief agency. We help people file for bankruptcy relief under the Bankruptcy Code. Assistance we provide with respect to Debt Relief may involve bankruptcy relief under the Bankruptcy Code."