I bought this in navy and light grey and was very impressed. I don't think much at all of Lands End cashmere these days but these are heavy and feel nice. Slim fit too.
Has the economic slump affected your shopping?
I have pretty much everything I need although that hasn't stopped me in the past - but I find I am tending to pick up smaller things like ties and sweaters at the moment, several from the excellent B&S forum.
If I were to consider a suit I would certainly think more about the purchase now than a year ago.
Italians often stick a large napkin into their collar, covering shirt, tie and everything. Looks a bit odd but works well.
I love wearing ties and I also don't seem to get food on anything. If you're dropping it on your tie and you stop wearing ties wouldn't you then just be dropping it on your shirt?
Grey flannels and brown suede shoes would look nice. Also mid-brown or maybe olive cords or just jeans.
I've always worn cardigans on and off and have just bought a navy (and a light grey) thickish shawl collar one similar to that worn by Daniel Craig in Quantum of Solace.
I wear them a lot at work after I've taken by jacket off and the temp goes a little low - no-one has ever commented and I wouldn't care if they did, not being interested in fashion.
Jacket and pants tailoring sounds about normal, but you are getting a bargain at $12 for the shirts, considering tailoring to fit makes THE difference. I find with pants I am paying bit by bit - eg $20 for tapering, $12 for hemming, extra for cuffs etc. I've had shoulders taken in and for a good job that's $100 to $150.
If the cost is not outrageous it is the best money you can spend. If something doesn't fit properly it will look like crap no matter how expensive it was.