Good looking and best trigger "right out of the box" got to be the Kimber. Am a fan of .45's and like most of us "pistoleros", once we fire a 1911, there's no turning back. My shooter friends's all have Colts, Norinco's, STI's and they are all great to fire.
This isn't your first pistol so, IMO, no need to figure out the 1911 platform slowly. With your budget, my suggestion is to get a piece that not only shoots well, but has the looks/value to go with it.
I like Para, but my smith doesn't. He would prefer STI, SVI or DW's. For STI, the Spartan shoots great, has a lot of features that are standard, but, IMO, for long term value, consider the Trojan instead for slightly more coin. Have fun shopping and post pics when you make your choice. Happy shooting!!!!