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

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The T5 definitely has better bug protection - they redesigned the floor attachment system and the seams are way more solid than teh older models. I've used both and the difference is pretty noticeable That said, if you're really worried about setup complexity, the Gazelle instant tents are still gonna be easier to deal with than a Kodiak even if you mess up some velcro alignment. Worst case you just walk around and double-check everything before you get in for the night 💀 Being anxious about gear purchases is totally normal but don't let it paralyze you - both tents will keep bugs out fine if you take 2 minutes to make sure everything's sealed up properly 😂
The T5 definitely has better bug protection - they redesigned the floor attachment system and the seams are way more solid than teh older models. I've used both and the difference is pretty noticeable That said, if you're really worried about setup complexity, the Gazelle instant tents are still gonna be easier to deal with than a Kodiak even if you mess up some velcro alignment. Worst case you just walk around and double-check everything before you get in for the night 💀 Being anxious about gear purchases is totally normal but don't let it paralyze you - both tents will keep bugs out fine if you take 2 minutes to make sure everything's sealed up properly 😂
Have you looked at the Gazelle T5 line? It is a higher price point but you shouldn't run into the problems you do with the insulated tents (ShiftPod, FSR, Overlandish). It had ripstop fabric and roof vents that zipper closed now. Like other tents in its category it has ports to run heating and cooling. Their stakes are petty good but I've been running the helical 12" stakes for all my tents. I always have my impact so driving then isn't a problem. For a little extra you can buy an insert that works with the tent and run a run a wood stove in the tent. I really liked that they came out with this version. I've ran several versions of shiftpod with our organization and while they worked we've switched our whole inventory to Gazelle.
Only downside with those is the size when taken down. Not sure what kind of car OP has.
A few years ago Academy Sports decided to use that same pop out technology, and now I have 2 *basically* [Gazelle clones](https://i.imgur.com/eiUXlrM.jpeg) that I paid less than $250 total. They are fking amazing tents. The blue one is my favorite. Butttttt Academy being Academy they never actually pushed it even though they are extremely awesome.
I've been considering a roof mount because mine make the bed a little awkward because I need to lay it diagonal.
We have a two Gazelle tents (one one-room and one two-room) and their gazebo. They are a breeze to set up and definitely not a gimmick!
I would suggest two tents then. We have a massive Gazelle tent and it is geared for 4-8 people but if I had to share it, I would only say four people comfortably with our stuff inside the tent too. It sounds like you have a pop up tent too? These will always be long and bulky because of what they are. Our old tent was very compact when packed up but was not a pop up and took longer to set up. My husband hates the size and weight of the Gazelle but it is the trade off of ease of setting up/breaking down that he gets for it. I think your idea to go bigger to fit more people inside a tent is not ideal if you are already worried about the size of your current tent.
I just use an Gazelle popup tent. Ample space. Can put a queen bed, pops up in 3m. Overland setups in/on truck are a pain in the ass. I setup camp and drive away often.
Isn't it AMAZING?!?! I went from being a backpacker to using this because I was mostly out of a vehicle as a rock climber now.. There is so much space, but it's still not overwhelmingly large.
I think your son would struggle with just about every tent given your description. A Gazelle hub tent is my recommendation. But you’ll want to supervise the rain fly attachment as the fly is a bit delicate.

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
Durston - X-Mid 2

Ranked #1
SlingFin - Portal 2