I image through 2 scopes side by side all the time. My reason is different as one is for spectra and the other is for simuiltaneous photometry but the process is the same.
I guide with the off axis guider on the spectrograph as the main guider.
If I want better guiding with the scope for images, it has an ST10XME on it using an AO unit. This will guide seperately within the limits of the travel of the AO unit. This takes care of any differential flexure and I have never reached the limits of the travel of the AO unit.
I use 2 separate computers. One a very old desktop running XP and a cheap lappy for the other camera. All fit on a little table easily. I then transfer the files to an ext hard drive for processing at my leasure on a more powerful puter.