I researched TheSky:TPoint:CCDSoft combination and didn't feel it was very well developed. Don't get me wrong, all three products are excellent, but the interoperability was of some concern even though they are developed by the one developer (Bisque).
I ended up going the opposite direction - MaximDL/CCD (which includes Pinpoint LE) and MaxPoint. As you're probably aware, MaxPoint is the equivalent of TPoint. What I liked about this combination was the ability for MaximDL to plate solve using PinPoint LE Astrometric Engine. Hence MaxPoint slewed to a star, MaximDL would take an image, plate solve it and then center it automatically. This would then be reflected in the MaxPoint pointing model. I've built a 120 star pointing model using this method with no problems to date.
The above is great, but what I really like is that every component is ASCOM compliant. MaxPoint acts as an ASCOM server (hub), so I simply point ASCOM clients such as - MaximDL/CCD,FocusMax,PolarAlignMax and TheSky6 (using the TeleAPI) to the hub. That way all programs benefit from the MaxPoint pointing model.
I recently downloaded the 6GB USNO-A2.0 catalog that contains 526,280,881 stars. I haven't had the time to build a larger pointing model with this catalog as yet, but it’s on the "to-do" list. I was actually impressed with the Losmandy Gemini Level 4 pointing model, but having used MaxPoint I realised the Gemini model doesn't deliver arc-sec accuracy across the sky. Not everyone requires this level of accuracy, but my goal is to establish robotic operations where I can image all night remotely. The observatory is two hours away from where I live. With no one at the scope to check pointing, software is my only option.
I think you're going to need a way to plate solve with CCDsoft to automate the process. You may wish to have a look at Pinpoint -
http://pinpoint.dc3.com/
I'm assuming you're using the automapper, if not... you'll need this...
http://www.newastro.com/newastro/dow...p2/default.htm