I am a member of a HealthShare organization. I understand that the contributions that I make are not deductible as a health insurance deduction for my sole proprietorship or as any kind of medical expense. However I have yet to see anything talk about HealthShare contributions being deductible as a charitable donation. If my HealthShare organization is a registered 501(c)(3), which it is, wouldn't the monthly contributions be considered a charitable donation for tax purposes, as long as I'm itemizing my deductions? Also, is there a way to write this off under the LLC's taxes? (Again, as a charitable donation and not as a health insurance plan provided to the company workers... me).