Going from point and shoot to DSLR is a big step up. The learning curve is very steep, and you have to make many investments in order to have the full experence. You have to investment a significant amount of money on the equipment and the time to learn everything.
If you’re the type that just wants to take a picture, stick with a good point and shoot. They have come a long way and are very advanced in a compact package. Some high end point and shoot camera now offer RAW images. RAW images are just that, raw. Cameras normally compress the pictures and manually adjust the photos before saving to a jpeg. RAW images allow you to adjust the image yourself.
I recommend getting the Canon Powershot G10, not the new G11, or the upcoming Canon Powershot S90. I’m glad to see that Canon brought back the Powershot S series. These are very good cameras with more manual controls than the SD series. For more information about the Canon Powershot S90, dpreview.com has a good initial hands on review. The Canon Powershot S90 is available soon. Expect a price tag above $400.
However, not all point and shoots are equal. Sure, there are cameras out there that only cost $100. But the picture quality pays for the low price.
If you’re the type of person that likes taking pictures, a DSLR is worth the investment. The picture quality alone is leaps and bounds above a good point and shoot. I am a little bias towards Canon. However, the Nikon D90 is a damn good camera as well. So it’s up to you to determine what type you are. There’s a camera for every type. Just go out and have fun.