generally speaking... freestanding tents are heavier than tents that need to 
be staked out. Freestanding + lightweight + big enough for 2 is going to 
require a compromise somewhere.    

I have and use regularily a Tarptent Double Rainbow, an MSR Hubba Hubba, and 
a Hennessy Hammock. All are great shelters for different situations. 

The Hubba Hubba is the most normal + all purpose but is easily the biggest 
(set-up and packed) and heaviest. I bring it when need to share with buddy, 
when weight doesn't matter, or when weather might cause me to "wait it out" 
in the tent. 

Dbl Rainbow is light, compact, and quick to set up (once you've done it a 
few times). It can be fussy as far as where you pitch it and how you orient 
it, but once you learn how, it works great and you stay dry. I use it mostly 
as a roomy (lots of floor space but not very tall) 1-man tent but it is big 
enough to share with my wife. If I was planning to share with a buddy, I 
would bring the Hubba Hubba.

The hammock has a learning curve. My first night in it was miserable. Now 
that I've been using it for a few years and have figured it out, it's my 
go-to shelter if I know there's going to be adequate trees to hang it from. 
My best nights sleeping while camping have been in the hammock.

If I were to suggest one based on what you wrote, it would be the 
Tarptent...  even though it's not free standing it's light + dry (if you 
pitch it right), and sturdy (I've been out in 2 impressive wind storms 
without collapse). I'd recommend getting the bathtub floor (vs no floor) 
option. 

good luck on the shelter hunt.

Smitty

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