The Mac OS is linux under the covers, hence indi runs on it. Yes, you could certainly run on Windows and connect to RPi running the INDI server. I run Ekos on a linux machine but the INDI server is running on RPi.
Many folk just run everything off the RPi incl Ekos and just remote into it.
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There is no shortcut to compensate for poor polar alignment as the mount needs to work harder to correct every slew both in RA & DEC. Whereas with good PA RA movement will be good.
I create a sequence in Capture tab which has 10 subs and save it.
In Scheduler there are tick boxes for Align, Focus, Guide and Track. I tick Track and align and load the sequence I previously saved. I set the Repeat for to say 10 which gives 100 subs. So what the scheduler does is before starting each sequence (10 subs) it does an align. So in simple terms...
- Align & Track, capture 10, Align & track, capture 10,.............
So in the course of 10 images if your object has drifted from centre its brought to centre again before starting next set of 10.
SGL has a lot of folk from UK & Europe so it never hurts to ask there.
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I used to be limited to 30s images before i added guider quite recently. I used to take 10 images of 30s and then force alignment via scheduler to correct for drift.
Join the SGL forum stargazerslounge.com/
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If its just the image name prefix that you are worried about, you can edit the name in the Capture screen before initiating capture. Thats what I do many a time as I'd rather not have a cryptic name like IC xxx which I later will struggle to relate to.
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Use your phone compass and point your mount in the direction of north pole as accurately as you can. Get started. Thats what I used to do too before I found a spot with views of NCP but limited views of rest of sky 
Dont get hung up on PA. You might not get perfect images but you will learn a lot about your equipment and software.
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That looks like a quite bare part of sky. Cant see too many stars in that region. If you just do a capture are you seeing enough stars?
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Can you post a screenshot of where you point your scope in first instance for doing PA. Not sure why legacy PA is not showing. Try reinstalling Kstars
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