You will get good at nudging the dob in no time Jowel. Good quality widefield eyepieces in your two most used focal lengths (10mm & 25mm) will help you no end, as the object will take longer to travel across the fov, so you won't need to nudge the dob as much. Just to note as well, the planets move across the fov a lot quicker than deep sky objects. I also use a Red Dot Finder, so if I lose things I can find them back much easier.
How about getting the 10" for now and adding an Argo Narvis down the track. Best of of both worlds

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All this said and done Jowel, I think you pretty much answered your own question when you expressed that you may get frustrated nudging the dob. This hobby takes quite a bit of perseverance & patience. If we don't have it to begin with, we end up acquiring it.
Have you looked into how much setting up an EQ mount involves? I just know that when I want to quickly get out there for a short session, my dob is ready to go at a whim. Drag it outside 30mins- 1hr before observing (to cool down) and that's it. When I'm finished, there's no packing up, I just drag it back in.
You've just got ask yourself what is going to be less of chore for you - setting up EQ mount or nudging a dob. The reason I went for a dob is because, I knew I lacked the patience to set up a mount and because of that, I was worried as to how often I would actually feel motivated to set it up everytime I wanted to use it. I now actually enjoy nudging the dob - I feel in control of my vehicle. Zoom zoom.
Nudging a dob will only be part of learning patience & tolerance... you then have targets to find as well... Though frustrating at times doing it manually, it is highly challenging and rewarding.
Kind regards,
Suzy.