Welcome Prophet. I think you'll enjoy your upgrade quite a bit
1. Not all that critical. I run them out to my tarp stakes. Not much tension: Take out the slack then an inch two for tension.
2. Webbing is pretty straightforward, but of course Shug has a video to help
https://www.youtube.com/watch?v=4cG0Ne_Ef5w Buckles make for a good/great water break, but I still add prussics to my continuous loops just in case. The head end water breaks are red, the foot end are blue, which is handy when my hammock is in it's double ended stuff sack.
3. That works. I leave it on the hammock and store stuff like stuff sacks and spare stakes in there.
General tips:
Foot end about a foot higher than head end is the sweet spot for most.
Practice setting up before you go on the trail.
Never hang higher than you're willing to fall.
Thinking you're sitting down in your hammock when you're really missing the hammock and sitting down in your underquilt/underquilt protector is practically a rite of passage, but can be expensive. The way the WBBB netting zips into the underquilt fooled me once. If only I had been in the habit of looking rather than just feeling with my hand before I sat down.
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