
The North Face
Wawona 6
Spacious vestibule, strong in storms, but rainfly tricky solo.

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The best bang for your buck when it comes to livable space, size and amount of pockets, ease of setup and teardown, and quality is the **Big Agnes Tiger Wall**, followed closely by the **Big Agnes Copper Spur**. I've tried literally dozens of tents and cannot recommend those enough. They are spendy, but when it comes to a freestanding tent that's durable and reliable, these things are really, really tough to beat. I see them all the time on thru-hikes like thet Colorado Trail, CDT, and PCT where rain / random mountain weather is common. A close second is the semi-freestanding **MSR Freelite 2 or 3**. It's also a solid, bombproof tent that's lightweight. My only real complaint about it is the cutout on one end effectively makes one narrow end a single-wall, which can condensate and get soaked in long periods of rain. But, it also dries fast, and ventilation is so effective it's rarely ever been an issue for me. Final recommendation if you want a non-freestanding tent is the **Six Moons Designs Lunar Duo.** Trekking pole tent that's budget-friendly, comfy, and just big enough for two people. Much more limited headspace compared to the above, but vestibules are large enough that I've never had an issue. Good luck!
I love my MSR Hubba hubba 2 person. The freelite is lighter, not as tough of a material. Both come in 1-3 person sizes.
I definitely struggled to get a proper pitch. It's easier with a trekking pole or adjustable carbon pole (the SMD pole is absolutely not the right choice it's too flimsy). I've had to reattach the front guyline, it tore off and the zippers seem pretty flimsy but that's par for the course with tents like this. The bathtub invariably lies flat at the back of the tent so I imagine you could get some water in there if it really poured but maybe that's to do with pitch. It's shape gives you some extra room but in practice it's fairly negligible because the back and side walls are sloped more than a typical mid. I thought it would be good for camping with a dog but the back wall is so sloped that there isn't really a lot of space for my medium sized dog (she pushes the back wall up with her back even curled in a ball). I don't think it's bad but by the time you include all the stakes it needs, and add up all the downsides I tend to just take my freelite (it only weighs a bit more and is way more comfortable/drier) or a dyneema mid.
I started using an MSR freelite one in my mix and I am quite fond of it. It's semi freestanding. It's gotten me through some severe storms and insects with ease.
I have the MSR Freelite which is a lighter and thinner tent than yours and have had no issues at all. I’m certainly not reckless with the tent but no one would ever accuse me of babying my gear.
Just a quick note, after Cubs when they get to Scouts there is no more family camping. So I would go cheap on the "family" tent for now, unless you guys are planning on using it yourselves for separate family trips. Most cub packs only camp once or twice a year. I got my son a three person MSR tent and myself a single person tent. The three person fit him and his buddy perfect. Those sizes are also a lot easier to hump to a camp site. I'd put the extra money in an inflatable pad to sleep on. That makes a huge difference. I used my old closed cell foam pad the first trip with my son and I woke up sore. The inflatable pad was so much more comfortable and kept me a lot warmer.

The North Face
Wawona 6
Spacious vestibule, strong in storms, but rainfly tricky solo.

Gazelle Tents
T4 Hub Tent Series
Fastest setup, durable, but bulky and awkward door.

Durston
X-Mid 2
Ultralight, spacious 2P, but not for very strong winds.

Durston
X-Mid 1
Budget ultralight 1P, spacious, but large footprint.

Naturehike
Mongar 2 Backpack Tent (Nylon)
Budget 2P, spacious for price, but not for 4 seasons.

Ranked #1
Durston - X-Mid 2

Ranked #1
Gazelle Tents - T4 Hub Tent Series

Ranked #1
Gazelle Tents - T4 Hub Tent Series

Ranked #1
Durston - X-Mid 2

Ranked #1
The North Face - Wawona 6

Ranked #1
SlingFin - Portal 2