If you're feeling generous, you might consider selling that Mod. 66 and "Pony" up $200 for a nice SS Colt 1911. Sure he'd be shooting more expensive ammo but he'd be shooting something he likes. Heck, you'd have a few bucks left over yourself.
If that idea doesn't float there's always the RIA for around $400. I've not fired one but I have shot a Citadel (its twin cousin) and it was a solid performer.
I stand by my original suggestion of a Beretta 92 or variant for an easy to shoot, reliable, inexpensive to feed and accurate pistol; at least worth a test drive.