You will have no issues with any of the medications or the accompanying items. Having nothing to do with the checkpoint, it always makes sense to carry a copy of all prescriptions because it can be difficult to get those filled if something goes wrong. A TSA Officer may ask to see those, but I would not be remotely concerned that he will and certainly would not offer it.

Make sure that you have a small collapsible bag inside one of your carry-ons. In th event that your larger carry-on needs to be gate-checked, you will still want to carry on the medical items, so have something into which you can dump them.

There are thousands of people traveling with insulin and other similar drugs every day. This is not an issue.