Well, lot's of interesting questions. I think my suggestion to you would be to start out by getting more experience in the outdoors during the winter months just doing dayhikes.
Shorter, gradually longer hiking trips will help you sort out a lot of your own solutions to these questions on your own. Especially those not tied directly to hammocking, but tied to winter outdoor recreation in general.
Layers...clothing is all about layers. When you get hot, layers come off. When you get cold, layers go on. When you're working (hiking) in the winter, it's better to feel slightly cold than overly warm...because if you're right at/just above comfortable...you're sweating and getting moisture into your clothing.
The only way to know how much layer to remove or add will be your own personal experience.
Carrying your gear also varies greatly. Pulks are great under some conditions...less so in others. Plan for the conditions you'll be out in.
Start out with some short day hikes, close to home. Take your hammock, carry the gear you intend to use...get used to it. Practice putting it up cold, tearing it down cold, using it cold. Figure out how much you sweat under what conditions, and learn what layering system works best for you.
THEN worry about trying an overnight in supported conditions. If it goes well...expand off that.