If you love your Glock, you may want to look into a 21sf. I had a shave/stipple job done on mine and love the gun. Incredibly reliable with any ammo I feed it, no muzzle flip, just a slight push backward.
As for 1911's, I'd suggest Springfield over Kimber for two reasons. 1st, Springfield's written warranty is for the life of the Gun, and I've had them honor it 3 times already, even going so far as to replace my gun with a brand new one. Kimber's written warranty says "1 year", and while they MAY honor warranties after that year, it's at their discretion whether they do or not. If you want a gun with a Busseian warranty, Springfield will have you covered.
2nd, and this is my experience, Kimber seems to be using stainless steels with a bit more carbon content recently. I was actually told this by a very competent gunsmith when I first bought my Stainless Pro TLE/RLII, but I didn't really believe him. About two months after buying the gun, I took it apart to lube it up and noticed some rust at the very front of the barrel. It wasn't a lot, but it was there. There was also so rust starting on the top of the slide. I worked it over with very fine steel wool and some BreakFree CLP and stopped the rust on the barrel from spreading, (the other stuff dissapeared) but I was VERY dissapointed with my 1000$ gun. Yes, Miami is a city with High humidity, but one shouldn't have problems like this if one is lubing the gun every 10 days or so and always wiping down with silicone. I sold the gun not long after. (Have left my Springfield in the safe for months at a time with no more protection than a coat of oil, a gun sleeve and a silica pouch, and not a spot of rust anywhere).
All of that being said, you also won't go wrong with the XD .45. Great warranty, 1911 Ergos and grip safety, melonite finish (comparable to tenifer) and relatively inexpensive. For your budget, you could get yourself a slightly used XD .45 AND a Springfield Loaded, then take your time and work on the Loaded til it is exactly what you want while having gotten to carry the XD.
