When it’s cold and rainy climbing into a hammock is like trying to right a canoe in the ocean. So let’s run this by the numbers…. It’s current 54F and rainy in Florida. I have my Outdoor Vitals 6 point tarp and OV hammock setup in the backyard.The tarp just barely covers the hammock. The side cat-cut exposes the ends of the hammock. Lowering the tarp closer to the hammock might create other challenges but this is what we have at the moment.People talk about dip lines and that might make sense too; but not implemented.In the meantime a pad is required to provide some insulation from the cool air. I’ve tried others and I’m still experimenting. Currently a klymit Inertia X. It’s torso length but has a few voids that let the chill get thru.A pillow of some kind is required for the same reason. I have many different kinds but I’m opting for a hydrophobic inflatable. The head generates a lot of heat so a quality pillow and/or beanie might also be a good idea. (not pictured)I do not believe in the high cost down products. The synthetics are as good and not effected by wetness. I’ve just tested the Klymit blanket and it’s comfy warm. It even has a foot box. My only complaint is that for the weight and fill level if the pad is not wide enough compressing the fill against the sides causes cold spots.And now for the canoe lesson.I put the pad, pillow and blanket in position. Took off my jacket and tried to get in. And in a flash everything was on the wet ground. If this was anything other than my backyard my gear would be muddy. Also when I took off my jacket I needed a place to store it. It ended up under my knees which was ok but any tossing or turning any it might end up in the mud.And as I was getting comfortable I was flopping gear here and there. And if I had my pack with me then it might be hanging from one end of the hammock catching water. While contractor bags might make good pack liners they blow away. So things get complicated.In my next test I plan to try a loose ridge line which I can hang a stuff sack or two. One for the ready blanket and pillow. One for my jacket. Alternatively I’ve ordered a gear sling from Sea To Summit. That will also be a place to store my gear at night.These technical bits make tent camping feel better but you still need to consider the season and comfort level. Not to mention that the hammock setup works on the ground too.UPDATE I changed out the Klymit Inertia for a Klymit Static V Junior. And the Klymit Versa blanket for a Snugpak Jungle Blanket XL. The systems offered about the same amount of warmth. I was comfortable for hours in my sleep/shelter. Closer to the end of the experiment the weather turned worse with a lot more rain and the occasional gusts. My backyard setup uses a tree and one hammock stand. so when I get in the hammock the tarp will sag a little. I added shockcord to the guy lines to keep the tension and with some tightening it worked fine. When I decided to call it a day I removed the sleep system only to find a puddle of water in the hammock.I have no idea how that got there as it was a puddle and not just wet fabric. I cannot say for all hammock fabrics but this OV should let the water drip thru. Also I did not see tell tail signs of a drip line from the head or tail. What seems clear, however, is that if I had been using the Inertia X then I would have gotten wet through the voids.