A couple of suggestions, some of which already mentioned above:
- Put the toiletries inside a clear plastic bag, one quart size. Have that easily accessible in your carry-on -- they will want to see it at security. Reason being, you don't want to be without that stuff in case your checked luggage gets delayed.
- Take travel size toiletries, making sure they're all under 3 fluid ounces each. They're not kidding about that limitation. If any item, no matter how innocuous, is over 3 oz, they will make you throw it away. Period. End of discussion. No exceptions. Begging and pleading will only make it worse.
- Really common knowledge, but you mentioned you haven't flown in a long time, so I'll say it anyway. No firearms or any related items whatsoever. No bullets. No magazines. Zero tolerance. If they find any of that stuff, you're not going on your trip....best case you're going to the police station, and jail is a distinct possibility.
- Sometimes people make jokes when they're nervous. "Looking for my bomb?" "You didn't find my Glock." Hahahaha. Don't do that. It'll be God's own hassle, and you'll be lucky if all that happens is you miss your flight.
- Also to protect yourself from lost or delayed bags, never have your medications in checked baggage. Always in carry-on. You don't want to be in an unfamiliar city or a foreign country trying to get a prescription filled, especially if there's some urgency around it. If the prescription is for a drug that bad guys can abuse, have the prescription itself, or an acknowledgement from the pharmacy, with you.
- For the plane ride, wear shoes that you can easily slip into and out of. They will make you remove your shoes at security, and you won't want to be wrestling with a bunch of laces or tight-fitting boots.
- If either of you have metal implants -- hip replacements, orthopedic rods, plates, etc. -- let the security folks know. They'll take you over and do a scan off to the side. It'll prevent going back and forth through the big scanner.
- For a lot of reasons, wear a minimum amount of jewelry. First, it makes security more of a hassle. Second, especially in a foreign country, it draws attention. You may or may not think of yourself as wealthy. To the local bad guys (and there are bad guys in every city in the world, domestic and foreign), you're a rich American on holiday. Make them view someone else as a richer, easier target.
When Mrs. Basket Case and I travel, especially internationally, the only jewelry we have is plain unadorned wedding bands, and that's mainly so she doesn't get pegged as a single female traveling. No other gold, silver, platinum, whatever -- no bracelets, no pins, no necklaces. No stones at all -- diamonds, emeralds, rubies, sapphires, nothing. Not even an engagement ring. The watches we take are almost toys -- a Swatch would be high-end by comparison. Nothing with any resale value whatsoever. Any good stuff gets left at home in the safe deposit box.
Sorry if all this sounds alarmist. It isn't. Travel is a great joy for Mrs. Basket Case and me, and we've been fortunate enough to do a fair amount of it. It's really about getting through security quickly and easily. Then, once you're at your destination, being aware of your surroundings, and making yourself inconspicuous as possible.