I shoot the Pentax K5 because it is weatherproof at less than $1,000 using the same SONY sensor as NIKON, SONY, etc. The image stabilization is inside the camera, which is a bonus since IS lenses tend to test worse than the non-IS versions. The downside to a serious amateur shooting Pentax is that there are more lens choices for Nikon and Cannon.
Sports and long stage lens: Pentax SMC-DA* 60-250mm f/4 ED [IF] SDM. Sharp wide open and weatherproof (it is a D*). There is a soccer mom shooting a BIGMA on my son's team, and this lens easily outperforms it despite the lack of reach. When shooting Little League pitchers you can often times read the writing on the ball depending upon the depth of field, which is narrow wide open. I wish I also had a 300mm or 400mm f/2.8, but this is so sharp why should an amateur bother?
All around lens: Tamron AF 17-50mm f/2.8 SP XR Di II LD Aspherical [IF]. I took a group shot of 72 kids on stage who were acting in a school play at f/4, and everyone was sharp in the 12" x 18" cast photos. Everyone wants a 17-500mm lens (LOL), but if you want corner sharp photos this is highly recommended by me.
Cheap portrait lens: Pentax M 50mm f1.7. This is an old "normal" manual lens I picked up for $40 on ebay that is fair at f/1.7 but very sharp at 2.8 on up. A steal among the old manual lenses. The old 50mm full frame manual lenses are 75mm equivalents, making them cheap substitutes for a portrait lens. They can be had for a fraction of the newer (automatic) $400+ 70mm to 100mm lenses .
Portrait and stage photo lens: Pentax SMC-FA 77mm f/1.8 Limited . I rented this at Borrow Lenses (www.borrowlenses.com) to shoot portraits and stage shots of 70+ kids in a school play, and it lived up to the hype (raised 2x more $ for the school than anyone before me). I definitely need a dedicated portrait and stage lens for all the volunteer stuff I'm doing, but can't find this lightweight 77mm for a good price. I am looking at the Sigma AF 70mm f/2.8 EX DG Macro as an alternative because it is much more versatile being a macro, just as sharp and less money although slower and much heavier. Both are full frame lenses, which is a plus. If only I had more money...
Fisheye: Samyang (Bower, Vivitar, etc.) 14mm f/3.5 . This is a manual lens sold under several names, relatively cheap and loads of fun. The depth of field is so great that I don't even mess with using Live View most of the time. I can't believe I lived so long without a fisheye!
Pocket Cameras: I recently experimented with the Pentax Q (IQ not great due to the tiny sensor), and borrowed the Fuji X100 (outstanding performance but out of my price range for now). My wife has an older Cannon that works fine, so that is what I use. I find the iPhone sucks for indoor shots and flash, but is surprising OK for some on-snow shots with post processing. It is better than nothing.
Software: Mostly Lightroom & occasionally Photomatix Pro (for HDR). If you don't want to mess with ND filters or a tripod and are only a couple stops off in either direction, shoot RAW and let Photomatix do the rest (or make the creative HDR stuff). Last night I fixed a photo from a hike last week to make a poster for my son's room, and Photomatix made a noticeable difference.