Pocket camera: Canon Powershot S90 (the recent S95 is probably even better). Takes the best photos I’ve seen from any camera that will fit in a pants pocket, and works pretty well in low light too, so you can shoot indoors without a flash.
Neck strap for SLR: Luma Loop (http://www.luma-labs.com/products/loop). Way more comfortable than a standard neck strap, especially for heavier camera/lens combinations, and really practical — easy to slide camera from hanging position to shooting position, easy to detach camera to hand it to someone else.
Digital SLR < $1000 (DX): Nikon D90 (upcoming D7000 should be even better). Great controls and hand feel, great set of features, great pictures.
Digital SLR, full-frame (FX): Nikon D700. Ditto what I said about the D90, except even better controls and even better pictures, especially in low light (high ISO). Heavy and expensive, but that goes with the territory for now at least.
50mm F/1.4: natural length fixed lens, fast for low light
24-85mm zoom: good zoom range for walkaround lens
70-300mm VR zoom: gets you close, zooms far out enough to leave on the camera most of the time
17-35mm F/2.8 zoom: super wide angle, fast enough for low light and background blur
35mm F/1.8: natural length fixed lens, fast for low light
18-200mm VR zoom: jack of all trades, good enough for almost anything
12-24mm zoom: super wide angle
Note that all the FX lenses work fine on the DX camera too, but the field of view is reduced, which makes some of them less useful. The 17-35 is a really useful zoom range on the DX camera, though, and with the reduced field of view, vignetting is not a problem.
This is all stuff I own, would buy again and would recommend.