If money was not an issue, here's my wishlist
Hammock: Blackbird Single Layer 1.7oz
Tarp: HG Cuben Fiber Hex Tarp
TQ: HG Burrow 20
UQ: HG Incubator 20
Cook kit: Trail Design Caldera System w/ Esbit
Winter setup would pretty be the same...living in So Cal, the winter weather here rarely drops below 0 and I think with the proper clothing layering system, the selected TQ and UQ combinations would work just fine.