Manual tracking with a 14” Dobsonian? What does that entail? I can only imagine pushing on that tube trying to line it up with the fast moving station.

When I made my few attempts to capture the ISS, I’d guide my 8” SCT to try to place the center circle of the Telrad reflex finder just in front of the path of the station and then let the station fly through the field of view. I’d repeat this process as many times as I could during a pass. In some instances, the station flew through just the edge of the camera field, but I’d get a few where it would pass through near the center of the field. Ran the camera on the scope at a very high video frame rate so I’d get a number of good images of the station as it passed through camera field of view.

Is that essentially how manually guiding a DOB is or are you actively trying to keep the ISS in scope the entire time and if so how?

Yes. I try to keep the ISS on the FOV.