I want to buy a nice hammock for my wife, who has only slept on the ground before. I thought I had a pretty good idea what to get, but once I start reading up again on all the options and combinations and mods and their relative benefits, I realize how little I know.
I would really appreciate if some of you with more experience could give some pointers.

She is 5" and 94 lbs, so it should be a light setup. We won't go out when we expect lower night temps than 35-40 F so I'm not sure if an UQ would be overkill. Most of the hiking year it should be around 50 F at night, up to 65 F at most.
There will be lots of mosquitos in the summer.

I have a Speer with PP and TQ, and I won't be needing the TQ (the PP is *warm*!) so she can use that in her setup.

I have a Speer WinterTarp, do you think that can cover 2 hammocks or should I get a larger one? Which one?

Finally, it would be great if I could get this under $400-500.

I was thinking that the Hennessy Ultralite + SS + OC would be light and nice, not warmer than necessary but she'll probably still need the UC the whole year. The included snakeskins look really nice, it takes me forever to set my Speer up...
But then I've seen some complaints about Hennessy build quality and the durability of the UC, and it looks like lots of people are selling theirs in the forum.

Speer doesn't seem to have many options available right now.

I also looked at JRB (perhaps The Nest would be nice), but they don't seem to have any lightweight hammocks.

What combination would you get for this kind of usage?

(If there's a decent ultralight couple solution I'd consider that, but I haven't seen any so I'm assuming that there are none!)