What's plate solving?

Yes, you can do it Paul. Depends on how hardcore you want to get i.e. your purpose for doing so. Plate solving has many advantages. I think a main one of yourself is planning an imaging session for guide star selection. As the focal length increases on-axis guide star selection can become a challenge. Using TheSky FOV indicators, you can determine the camera orientation to pick off a guide star. Then, when at the telescope, when you plate solve an image, you'll be able to match the camera rotation to nail the star you originally planned. This is simply one of the many wonders of using plate solving - there are far too many to conclusively list here. Comes down to what you want to achieve. I agree with Fred that is typically used for robotic/automated set ups to control actions such as pointing or focusing, but don't agree that its grief ridden. You do however need to be software savvy. I've contributed to a few threads in the past,
heres one and helped others along to plate solving nirvana. Given you've already got TheSky, I'd simply use CCDSoft for data acquisition based its tight integration. The two will provide the plate solving service with a camera that writes out in FITS format. I would suggest you get all the key factors such a general telescope pointing, focusing etc under control before you embark on getting plate solving running. Sounds like you'll have a steep learning curve with the new camera to start with. You'll have a little fun determining the integrated guide port offsets to getting TheSky FOV indicator correct I suspect, though not as difficult as the Astrodon MOAGs. Anyway, yell out if you get stuck.
Cheers