#1 Yes you need to use each year's program to amend that year. I assume you used Turbo Tax Premier (not Premium). I use the Home & Business program so I'm not sure where you enter it. But you can search for schedule C. It should be in the same area you entered your self employment income and expenses. There should be a spot for Retirement and Health Ins.
#2 Do you pay the Medicare from Social Security checks and get a SSA-1099? Go to the SSA-1099 entry and delete it from the SSA-1099 entry screen. Medicare plan B payments are qualified as Self-employed medical insurance premiums and should be entered under Business instead of in the SSA-1099 Social Security Benefits section.
Try this for where to enter it. https://ttlc.intuit.com/community/entering-importing/help/where-do-i-enter-my-health-insurance-premi...
#3&4 Sorry no you can not efile prior year amended returns with Turbo Tax. Mail each one in a separate envelope. You don't have to wait for the first one to be processed.
