Be aware that you can also reimburse yourself retroactively, as long as the HSA account was established before the date of the medical procedures. For example, if you were to pay $20,000 out of pocket and you only had $5000 in your HSA, you could reimburse yourself the remaining amount by depositing money into the HSA (up to your annual limit), getting the tax deduction, and then immediately withdrawing it again to reimburse yourself for the previous expenses. With the single limit of $3600 per year or the family limit of $7200 per year, it might take you several years to fully reimburse yourself, but you would eventually get a much larger tax benefit than if you took the items as a deduction on your federal return subject to the AGI limit.
You will also want to maximize your contributions into your HSA if you know that you have a large upcoming expense. Your contribution limits depend on whether you were covered by a self only or a family insurance plan and whether you are over age 55.
