Background:
I got my CHL four years ago and am up for renewal in 2009. If I carry, I usually ankle carry a small S&W revolver. If I'm wearing shorts (which is admittedly most of the time), I typically carry a semi-auto in a full sized backpack and keep the revolver in my console. If I'm wearing slacks, then I'm wearing boots and my ankle holster won't do, so I'm either doing the backpack or nothing.
I am convinced by the "carry 24/7 or guess right" philosophy, but I don't back it up because I've never found a comfortable way to carry. I work from home, so I'm really not out that much. My wife has a CHL and normally carries a small S&W revolver in her purse or in the diaper bag. When she isn't doing that, it's in the console of her car.
Our home defense plan is solid, but the roaming plan needs to be shored up.
Firearms:
All of these were purchased with the intention of carrying. I'm a fairly big guy (6'5" and 330 lbs. - wear XXXL or XXXLT), so carrying the P229 IWB didn't last too long since I need most of the available real estate inside the waistband for myself.

Eventually I'd like to get a Kimber Ultra Carry .45 ACP, but that'll be a while considering our recent buying spree to pick up an AR and investigate tactical shotguns before the end of the year. I really just need to clamp down and commit to one of the options I've already got until I can buy a more suitable subcompact.
Kimber Custom II 1911 .45 ACP w/ Wilson combat mag
Sig Sauer P229 double/single .40 S&W
Smith & Wesson 640 .357 magnum/.38 +P/.38; stainless steel; 5-shot revolver with internal hammer; DAO :: This is the my normal ankle-CCW
Smith & Wesson 340PD .357 magnum/.38 +P/.38; scandium alloy frame with titanium barrel; 5-shot revolver with internal hammer; DAO :: This is usually loaded with .38 +P and is my wife's primary CCW
My thoughts:
I've leaned toward carrying the Kimber IWB or with a snug OWB holster (I almost always have my shirts untucked). It's heavy, but it's slimmer than the Sig P229. Carrying the Kimber or the Sig would allow me to still use a revolver as an ankle backup.
It just recently hit me that I could get an IWB or snug OWB holster for one of the Smith & Wesson J-Frame revolvers, too. They're only five shots, but the waist carry would give me better access to the firearm and allow me to carry on my person even in shorts or when I have on boots.
And, like for most people, money is tight. I have a problem picking a holster because most of the good ones I've seen are online, too expensive, and there's no chance to walk around and see how they really feel before purchase. Cheaper than Dirt's selection is terrible, and I've been largely unimpressed with the options at the High Caliber Gun Shows in Fort Worth.
The questions:
What would you recommend as the carry option out of my existing inventory?
What specific holster (links appreciated) would you recommend?
Any other advice you want to throw in. . . go for it.
Thanks in advance!