Mailings depends on how the office runs things. If I have a balance due and I guess depending on when they run accounts due, I think twice I got a statement. Most times I am awake enough in the morning to remember a check.
Unless you have a ton of medical expenses, don't worry about taxes. Basically unless something catastrophic happened or major surgeries, you will never meet the deduction limit which is MUCH high than the limit for itemized deductions.
Both of my therapist code the visits appropriately, Depression and Anxiety. Like what trans person is not depressed or does not have anxiety? So far my med insurance has not bounced the hormones. Most insurance policies do have an exclusion for transgender related services. Docs who see us are mostly aware of this nearly universal policy