No suggestions from me, unfortunately it's been far, far too long since I've been shooting or investigating, but didn't some court just declare the conceal carry stuff magically unconstitutional only in St. Louis county?
I'll have to check on that. I saw that St. Louis City wasn't issueing permits, but that's a very different thing.
My suggestion - start them out with open sights. After they've learned how to aim and shoot using them, then go to a scope. Each is a technique all its own, but it usually easier to go from open to scope than it is to do vice versa.
Mike from Oregon's advice is hereby seconded.
There are many good .22 rifles but the king of the .22 handguns is the Colt Woodsman. My Dad owned one in the 1930s and loved it.
(There's also a funny Kerry pic on the page)
The Woodsman is a semiautomatic target pistol usually chambered for the .22 long rifle (LR) cartridge. Many of them have a slightly sinister Lugerish look to them. AFAIK they are no longer made but used ones are available at about $500. Hit Google.