Are you already well-trained on those? Me, I'd tend to think you have enough hardware and should invest in software. I'm NOT a trainer, no conflict of interests or motive in my recommendation, and if you're already investing in software and just have that much cash that you can do plenty of both, then get a nice full custom 1911 made.
Another would be a Detonics MTX doublestack 1911 with modern ergonomics to make those Kimbers feel really old in his hands.
Sticking with a the 45acp, a CZ97 would be a great choice, or a CZ75 if he wants 9mm. While not common in the US, it is rapidly gaining popularity here and the CZ75 already is used by more police and military than the Glock.
If you're looking for something "next level", the P7 series by HK is probably right up your alley.
Standard P7s (no heat shield, Euro/heel mag release) are the least expensive ($700-800). The P7M8 is a step up (heat shield + push-button mag release). P7M13 is a double stack version. The P7M10 is a double-stack .40 S&W. You won't touch a M13 or a M10 in your budget, though...
If you DO go this route - search out a package that has as many mags as you can find / afford. They're SCARCE. And EXPENSIVE.