Sounds like a very good setup to me and I'm sure you learnt a lot from your previous trip. The hammock is a bit risky though! maybe it will be hard to sleep in or at least a bit cold!? Will your face have to be covered at night to stay warm and if so won't that make it a bit less comfortable and harder to breathe? I suppose an important point is that with a bikepacking trip you can always throw things away or buy new things along the way. Just make sure you get some decent frame bags because they are a specialty item that can be hard to replace if broken, unless you are in a big city.
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The warmth of a hammock actually not that different from a tent, unless you have a 4-season tent. You will be a bit more exposed to wind but the tarp will take most of it and with proper isolation from below you will be nice and warm. Of course my face would have had to be covered if i was to sleep in the winter period but I dont intend that just yet. But from early spring and onwards a hammock is superb. I have slept in it down to 0 degrees without much trouble and back then I didn't even have proper gear. I have seen ortlieb are now selling frame bags, they look solid!
With the gear I took on my trip it was very cold at night when the temperature dropped below 10 degrees but maybe that's just because I didn't have warm enough equipment. It also probably didn't help that I was in Belgium and northern France. Where are you thinking of going on your next trip?
I was in Norway so that's as north as it gets almost, haha. It's all about equipment in the end. For example my underquilt(a thing you hang below hammock for warmth) got a comfort temperature at - 7. Probably starting out to take eastern Europe, maybe from Denmark to Romania to start out with!