My husband and I have the same problem as nytony going through security; we both have knee replacements and I may have plastic or metal screws in my toes.
First, night before we leave we stay at the hotel and the next morning , we take off all of our medic alert bracelets, watches and don't wear any jewelry. I have a personal bag like a satchel; in that I put a purse that is lightweight and that has my medications in, and I'll use this on the trip . After checking in at the Ariline desk for boarding passes/baggage check-in, I take my boarding pass/passport case off my neck and put it in the satchel or purse, mostly a zipperd compartment. I keep the passport and boarding pass in my hand. The purse zipper is left open, the satchel zipper partially open. I go through the preliminary desk where the guard looks at the passport and boarding pass. I ask if I need the passport to go through the screening. I am always told NO, so I quickly put my passport in the purse, zip it up. If I have time, there is a lock on the purse and I will lock it, but not always possible, and zip the satchel as well. I have already taken off my jacket (it's warm here anyway), and put it on top of my purse in the satchel. Then when I get to the trays and take off my shoes, I don't have anything in my hand except my paper boarding pass. The satchel and my wheeled carry on are the only bags on the conveyor plus the gray box with my shoes. So, anyone going through my bags has to work at it. I am always screened and patted down, sometimes our handcarries are sitting at the end of the belt at least 10 minutes while we are being wanded. Yes, I worry, but I keep my eye on them as much as I can. Sometimes they want to see something in my satchel or my husband's small duffle with cameras/netbook. They wait for us to finish being wanded. But the guards are always laughing and talking, so that doubly worries me about the bags.
We did try doing what nytony said, one going through first. That means the second person has to have all the bags/wheeled cases for both of us going through the belt. Then the second person gets screened, the first person picks up all the bags. Sometimes Security is confused and thinking we are taking someone elses bag, but it hasn't been a problem when we did that. But, we haven't done that in a long while. Most of our flights are early in the morning when we depart on vacation, so there aren't a lot of people around and security goes fast then.
In May when we were going to Ireland, my husband, being sometimes harried,, forgot to put his passport in his small duffle after the initial security check , carried it in his hand, they made him put it in a box, luckily his box with shoes was not yet through the screening; he put the passport in there, but when he got his shoes, he forgot to pick up the passport. I realized right away and rushed to the belt end and asked the guard. It could have been pretty bad had we not noticed it. I now try to keep an eye on all of our stuff. That's what I meant in another thread that we may have to re-think traveling due to medical reasons.
Each person/couple has to do what works best for them. I traveled for my job about every 4-6 weeks by plane for 5+ years;, so I tried a lot of ways, and the way we do it now works best for us.