Hello Coach...I recently went through this dilemma. I used a Kodak DX 4330 for about 3 years. Then I upgraded to the Nikon Coolpix 8400. I loved it, but then I purchased a Pentax *ist DL for the wife. That was it...2 weeks later I bought me one.
I found that it was actually easier to use than my 8400 and much faster. I have had a few problems with keeping the sensor clean and even had to have my wife's sent to the factory as a piece of debris got somewhere that couldn't be cleaned manually. My picture taking has improved slightly because I find myself using only manual 99% of the time. I still carry my Nikon and my Kodak, but mostly for backup and to let the grandkids use. However, I upgraded mainly for the ability to have more zoom. Unlike your 8800, my 8400 only had 3x zoom...but it does have the 24mm lense which is great and offers me some flexibility combined with my Pentax. It really all comes down to how far you want to take your photography. If you want the flexibility, then upgrade to the DSLR's, if you like the convenience of the p/s's, there are pros out there who only use p/s's. Don't think that upgrading is necessary to improve your photography. It's the nut behind the camera that creates the masterpiece, not the camera.
Ken