With Tarptent, the Stratospire 2 is a 2-person, double wall tent. The Rainshadow 2 as a 3-person single wall tent (with this specific tent, "2" refers to the model number, not to the number of persons.) They also have the Cloudburst 3 which is basically a tunnel tent (you can add a third "rib" in the middle for greater wind resistance). It also has a liner you can add to reduce condensation. With the extra configuration (third pole and liner) it should do fine in winter. Their Scarp 2 is a two-person, 4 season double wall tent which would be fine for winter. Their Hogback holds 4 and is a 3 season, double-wall tent.
Of these, I have the Rainshadow, which is palatial for two adults plus dog, and plenty of room for two adults and a kid---some have even slept two adults and two kids in it. It will take three adults but is a trifle cramped at the sides. I've had no issues with condensation in it, even at the Olympic National Park beach in fog and drizzle. It is quite weather resistant as long as you use the "optional" side guylines and keep the foot of the tent pointed into the wind. You do not want this tent for winter camping, though.
You can get large pyramid tents from Mountain Laurel Designs (their "Circus" tent), Oware or GoLite. With those, you'll need an inner net of some sort to keep off the bugs.
Lots of two-person tents out there. The lightest is probably the new ZPacks Duplex tent, 21 oz. including stakes. Of course it's made of cuben fiber so is way, way over your budget.
Important: If you're using the tent in the winter, it needs to shed snow easily and stand up to quite a bit of weight from said snow and generally higher winds than a summer tent. The heavier tent is not for warmth (it really isn't any warmer) but for the needed strength to withstand more wind and at least 6 inches of snow without collapsing. Pyramids are good for this as are tunnel tents.
Edited by OregonMouse (12/02/13 07:10 PM)
May your trails be crooked, winding, lonesome, dangerous, leading to the most amazing view--E. Abbey