How do I claim multiple insurance plans through a single year along with having paid a deductible for surgery as well as out of pocket expenses?

Under the Health Insurance section, indicate that you had health insurance for all of 2017. Then on the following page indicate that you had the Affordable Care Act insurance and continue with the interview questions. Enter your 1095-A (upload or type it in).

You will not need to enter any specifics for your employer plan in TurboTax. The out of pocket medical expenses are deductible as an itemized expense if the total of all of your medical expenses for the year are greater than 7.5% of your adjusted gross income. You can enter all of your medical expenses to see if you have enough to deduct in the Medical section.

See TurboTaxTeresaM's answer below for reference.

https://ttlc.intuit.com/questions/3865996-how-do-i-enter-health-insurance-coverage-from-multiple-sou...