What I am wondering though moving forward - what would be a good way to quickly assess if adding additional data is still making a difference?
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Or put differently: how are the more experienced imagers handling this? If you have collected a certain amount of data but feel you need more, would you still go through the whole process just to check how the already obtained data looks like ... even though you already know you will collect more in the near future and thus have to start right at the beginning again?
More experienced imagers: we use our experience. 
I've got a feel for what another hour will add with my set-ups. Also, I image a lot, so I can go long. Basically, I image for as long as I have patience for that object, or the trees/twilight get in the way. I am usually getting 1-3hrs per object per night, then over a few weeks, factoring in the moon and occasional California clouds. On my long f/l rig, I have to take into account seeing, so may skip there if that's really bad.
I preview the stacks (over multiple nights) in NINA. That gives me a general idea, but not full processing (and mono only, for me).
Then in WBPP, on my processing days (used to be weekends only, when I was working), I will generally stack selectively (as in, whenever I feel like it, not every night), the whole image series to that date, automatically preserving the master calibrations in WBPP. I am impatient to see what I'm capturing, so I do generally stack 2-3 times before final over the weeks, but as I build experience, I don't need to stack as often. I know to typically look for 10-20hr per target if possible in my Bortle 4-5 skies, though circumstances may vary that -- I've done over 40 for some targets and less than 4 for others. This is my experience, the object type, my interest in the object, and my local conditions.
I'm semi-permanent, so I don't re-take flats unless I change the imaging train (which is every few months). If you have to set up every night, then sure it's best to re-take flats, and then use the keyword/session technique in WBPP as Dave mentioned.