I have used both on September sheep hunts in Alaska. Long story short, I prefer the SG Skyscraper for 2 people. Details below, and kind of a repeat of what others have said.
Hilleberg Anjan
I used an Anjan 3 for two people. If I recall it is 3 oz heavier than the anjan 2 but has more headroom and width, which is nice if you have a weather day or you end up with a gear bomb. It’s a Hilleberg, a nice capable tent for the weight. It withstood strong winds even after some of the guy line stakes got ripped out.
Pros:
weight for 2P (4lb 3oz)
Hilleberg durability
high denier and WP tent floor no need for footprint
ability to pitch a true fly first and keep your inner tent as dry as possible in rain
Cons:
vestibule size and location - This is manageable but definitely not ideal. The vestibule is in front of the one entrance to the tent, so getting in out can disturb your partner, also not a lot of room in the vestibule to leave gear laid out with 2 people to exit tent. GT model would help with this but would make footprint longer, see below, and add weight.
Dimensions/pitch style – these are related. It’s a tension style tent and pretty hot dog shaped (63” x 127”). So you need a long flattish area to pitch and pull it tight. If the tent isn’t taught its not going to be able to withstand as much weather. Being hot dog, there is an optimal wind orientation - that being said we have pitched it the worst way possible and it held up in high winds.
No apex vent – being a hilleberg yellow label that is no apex vent and it relies on air circulation from under the fly. This would most likely be fine in august, but my last 2 hunts have been in September with way more humidity and experienced a lot of condensation build up in the tent. Bring a sponge (but you should do that for any tent)
SG Skyscraper
After the above experience, hunting partner and I wanted to go with a 2 door 2 vestibule tent (your gear on your side my gear on my side, each have our own door). Considered Hilleberg Allak 2 (7 lb 4 oz, $1165) and Rogen (4lb 10 oz, but more expensive) but took the chance on the SG after a friends review.
Pros:
Cost (relative to Rogen, $645 vs $1055)
Slightly taller than Rogen, 41.5” vs 39”, this is noticeable. Also the web truss system really pulls the head space out so there is plenty of room for two people shoulder to shoulder on a weather day.
2 door 2 vestibule is a really nice creature comfort, bigger vest than Rogen (11ft2 vs 8.6ft2)
Surprisingly bombproof in the wind. Pitched it was pretty stout but when we put our poles under the short webtruss arms and tensioned it this thing was rigid on all sides. Was really impressed. And it withstood 60+ mph winds even after we tore the rain fly zipper (operator error) earlier in the hunt. Tent is very symmetrical, hamburger shaped, so resistant to wind in any orientation, but mind the doors
Lots of pockets and strings for drying gear
Apex vents for minimizing condensation, but still bring a sponge
There is a ton of optionality with this tent, fly only, inner only, etc for other hunts or keeping weight down for a roomy 1P
Cons:
Inner tent floor is only 20D, we never had an issue but used 3mm plastic ground sheet
Not a true fly first pitch, as inner and outer need to be connected for pitch to get shape of tent poles. You can keep the inner protected and separate for part of assembly/disassembly but it’s a little bit of a hassle feeding tent poles through the wet webtruss. Hillberg wins here.
Footprint is nearly as long as anjan, 92” x 118”, shorter but wider. still need to find right pitch location
Fly and floor WP rating is less than Hilleberg, but we had no issues in rain or snow
7oz heavier than Rogen, 14 oz heavier than anjan 3. Skyscraper is 5lb 1 oz.
Fun fact about the skyscraper, it is designed by SlingFin tents, very similar to Sling Fin Crossbow.
