Holsters first. For concealment, IWB is less comfortable, yet lower profile. I like Kramers IWB holsters and have carried a Delta Elite in one quite often. Will soon have my Lightweight Commander back and carry it. For outside the waist band, I like my bianchi shadow and have also used a kydex holster by Blade-Tech. I have one of the new Uncle Mike's kydex holsters, and find it superior to the blade tech. It holds the gun in position better and more comfortably, and has better retention.
As to the gun, there are so many options (unlike the Glock, eh? I have a couple of them, so I can say that) for complete guns, custom guns, etc. It really depends on what you like and what you want to use it for. If a few hundred dollars is standing in your way of getting what you want, keep saving. It'll be worth it to get what you REALLY want. You will pay more, but you'll cry only once. =)~
STI's Trojan ($1000) is a great value and needs virtually nothing. Impeccable fit and finish. Don't care for the rollmark, though. STI's customer service is very good.
Springfield's TRP ($1250 to $1350) is another contender, but has that ugly "TACTICAL" on the dust cover. From what I've seen, Springfield's customer service has a great reputation, unlike Kimber.
Kimbers are good base guns, and the high end kimbers are good, yet sometimes need someone who knows what they are doing to tweak them a little.
Baer's guns are well built, and beautiful. People rave about them. Customer service is supposed to be improving, and I've seen posts of extrememly satisfied customers when they needed something fixed.
If you really want a Wilson, it's not that much more than $1500.
Of course, there are few things so fine as a truly custom 1911. One setback is that that the many of the good smiths are backlogged. Quality is a consideration, so is delivery time. I've waited from 3 months to 3 years for guns. In each case, the wait was worth it, but I had other guns on hand that I could shoot.
In choosing a smith, talk to them first. Tell them your wants/needs/questions and let them tell you what they think. In most cases, they will give you good advice and you'll be pleased with the end result.
A few smiths who immediately come to mind are Dane Burns, George Smith at EGW, John Yanek, Mark Morris. Shops include Wilson, Baer, Springfield Armory's Custom Shop.