"I have the Humana Advantage plan (over 2 years now) with a HIGH deductible. My social security check automatically takes the premium for this policy. Can I reimburse the premiums to myself from my HSA? I want to roll the money over from the HSA to my ROTH."
You cannot roll HSA funds over into an IRA. To avoid penalties or taxes, once you contribute money to an HSA it must stay in the HSA, be used for qualified medical expenses or be rolled into another HSA. HSAs allow you to reimburse yourself provided the funds are used for medical expenses.
What qualifies for a medical expense depends on the definition presented by the IRS in Publication 502. Being on social security usually makes health insurance qualify as a medical expense, making it likely that you will be able to receive a reimbursement. For more information on what qualifies as a medical expense, click here.