I'd definitely echo the sentiments about getting out and seeing other folks scopes, those that are similar to yours are just as important just to see how different people tackle the challenge. Sounds like you've got a good scope already, but it often helps to get hands-on experience and a little help from others.
Moving to a SCT is an expensive exercise from where you are now...I say this as a SCT owner and user, with a Nexstar 8 and a C11 that I (occasionally!) mount on an EQ6. The 8" is great for grab and go, it's light, easy to setup (like the CPC) and has decent light grasp. I've always wanted a CPC but they're expensive and heavy. I use the EQ6 for the 11" because it breaks down into more manageable sizes and weights, but the setup is a little more complex and takes a few minutes more...the views are usually worth the effort though
Regarding focal length, it only matters if it matters

depending on the objects you're interested in, it may not be of detriment, but you would probably need to add/remove an eyepiece or two because of the difference in focal length. With a longer focal length eyepiece, you can get about a 1.1 degree FOV from a C9.25, more if you bung the reducer on the end as the focal length becomes more like your Dob. For really big objects, a pair of binos or a short focal length refractor is most likely a better fit, and also doubles as true grab and go