For the hammock, take a look at the warbonnet XLC. One of the bigger/taller guys in our group swears by his. I've got the classic 1.1 double layer blackbird (I'm 5'11"), and he was close enough to the max that he opted for the xlc with 1.7 fabric rather than mine. Same basic design, however. The double layer has a nice pocket/pouch for an air mattress and adds some extra support. Both have bug netting built into it.

In Minnesota, I'll use my neo-air with a bag/quilt in the 25F+ weather. If it is going to be under 15F, I use an under quilt.

Tarps are one area where you can expand as time goes on. The blue polytarp is cheap, but heavy. You could strap it to the outside. I've really come to like my cuben tarp. Just a handful of ounces and packs down to a reasonable size. My superfly packs down to about the size of a tennis ball can, and fits somewhere between the polytarp and cuben from the dollars/ounces category.

I'd seriously consider a bigger bag, or a small secondary shoulder bag. Consider the VC 60 - a 60L/2.2lbs pack. The top rolls down and compresses, so there won't be much bulk. Under 20lbs, it is pretty comfortable. In the 10-12lbs range, it is fantastic. This is as small as I can fit into when I winter camp. I can also fit a hammock, tarp, and mattress inside a small map bag. Something like that would free up room in your current pack for the sleeping bag and some extra sox.

Lots of good info on Shug's channel, if you like youtube format.