I started my photography journey with a point and shot Canon Ixus and soon moved into a bridging camera - a canon S3IS, although back then i don't know if that is what they were called? Now have a Nikon D7000 with mulitple lenses. If you want Nikon information I can help with that. Don't know much about the current canon line up but its easily researched.
I was always a canon shooter (before my Nikon days). When I purchased my first DSLR the Nikon D90, I had a big decision and was comparing the Canon to the Nikon. Both, at the time, were roughly the same spec and image quality. What swayed me was the quality of the kits lenses. At that time nikon, from my research, had the better quality kits lenses and this is why I changed brands on what I believe was a very important purchase.
As others have said, you need to identify what you are going to be taking photos of primarily. The biggest thing with switching into a DSLR is the weight and bulk side of things. I have a friend who purchased a wizz bang DSLR for thousands of dollars because he believed he would get awesome photos by having a high spec camera. This is certainly not the case. The higher the spec the harder it is to get a great photo as you have to be more technically minded with the camera. If you get a DSLR and always have it in Auto mode, you might as well have a point and shoot or bridging camera as the quality of the pics is going to be basically the same and you have spent a great deal of coin for no real benefit except lugging around a bigger camera.
If you want to see some images I have taken check out my
blog. Im happy to share any info i have.

Just my two cents worth anyway. Good luck with your purchase.
Ants