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Being married to an aspiring photog who has both DSLR and point-and-shoot, I've had a chance to play with both. If might offer a couple examples...
Nikon D200 w/ 50mm/f1.4 "prime" 10.2MP (about $1800 camera body + $50 lens) Local Motors Rally Fighter shot taken up close without a flash.
 Full size image (huge) to show image quality: http://mitsubishi.gearboxmagazine.com/Brian/VJD0346.jp g
Nikon S220 point-and-shoot 10.0MP (about $180 right now) 195/2000 in the garage (shade) during the day.
 Full size image (equally huge) to show image quality: http://mitsubishi.gearboxmagazine.com/Brian/195-dash-removal-026.jp g
If you compare the full sized images linked above, you will notice they're almost the exact same size, but the one taken with the DSLR has much finer detail. This is a function of the larger image processor mentioned in the article pasted above.
At the same time, notice how the resized images are relatively close in quality. Yes, the Rally Fighter is more photogenic and the composition is better, but if you look at light, shadow, contrast, and depth of field, you'll see they're pretty close. (EDIT: The Galant is painted flat black, has about 12 months of dust all over it, and I was smoking a cigarette when I took the picture.)
The S220 is a piece of cake to use, but you can run into it's limitations from time to time. When the lights get low, you'll still want a tripod to snap the best shots without a flash or you get blurriness. Even so, while the D200 can take some incredible shots without a flash, much of that has to do with the "nifty fifty," fixed 50mm lens I used.
A point-and-shoot will have you covered for the majority of your picture taking needs if you're wanting to document hanging out with friends or sharing the random picture of your car online for ride of the month or a calendar or something. More often than not, it's a piece of cake to use and get good pictures.
The DSLR, on the other hand, has more bells, whistles, and settings than you can imagine. You can take a picture of the car from one end and have it turn out spectacular, but when you take a picture of the same car from the other direction, the picture looks like complete shit. My wife's DSLR has more settings than Megasquirt, I tell you.
So, if you're looking to take pictures of good times with friends, the car out and about, don't want to spend an arm and a leg or have to obsess over camera settings all the time, get the point-and-shoot. I highly recommend the Nikon Coolpix line. They're small, light, take awesome pictures, and don't cost a whole lot.
If you want to take professional quality shots that you could print out on photo paper full sized for like a framed 8x10 for grandma, or want to seriously get into photography with the option of buying super awesome lenses (which can cost upwards of $1800, depending on what you want), then start comparing features and benefits of the DSLRs. I don't know that I would suggest starting with the Nikon D200, as it does tend to struggle in low light situations, but a D40 or D80 would be a good start and keep your entire kit under $1000 imo.
Hope this helps.
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