How strict is tsa for American?

I will delete anything negative I am just curious and need some help. I take Xanax as needed but no doctor will prescribe them. I get some from a friend every now and then. Will tsa confiscate my medication without proof of prescription? I also have a ton of other meds but all over the counter and have prescriptions as well. I’m terrified of flying. It’s my second time within a couple years or so. I thought I was going to die and throw up at the same time lol. Can I put them n a day to day thing with everything else or just don’t take them at all? Last time I flew I didn’t have any medications but since then I have gotten really sick. Been sick for awhile but no doctor can figure out what’s wrong with me. Plus thousands and thousands of dollars just for the tests. This flight is a birthday/Christmas present from a friend. I don’t know much about flying at all. Last time I was even late getting there 2 hours early cause I didn’t know where to go or what to do. Someone told me to get in the wrong line so I had to start all over and missed my flight. Also do you have to pay extra for wheel chairs at the airport or just request them? Last time I could barely walk and missed another one of my flights but later on for the other layovers and such I got help.