First of all, You are asking all very good questions.
1. I would strongly reccomend the Otter as far as brand. I strongly believe that you “get what you pay for” and the Otter all around is straight up a 100% quality house that is built to last. I can say this, as I have owned an Otter Wild series and recently updgraded to the Otter Pro Lodge(Insulated). I sold my Otter Wild series after 4 years of use and it looked brand new and the sled was in great shape and that was even going down some tar and gravel roads when I had to. The guy that bought it, did not even hesitate. I did not have the hyfax kit on it either. Anyway, my point is that you will never in my opinion wear out the sled on the Otter. All of the Otter sled are Roto-molded which means that they are not pressed out of one piece of plastic but baked in a mold from a powder. I am sure you know what Roto-Molding is however, until I got to see the Otter factory in action- I had wondered what it really meant! If you also look at the front angle on the Otter sled it is designed to go over snow not push it like some of the other sleds out there. The sled also has a pre-fabricated hitch system that is a huge bonus that I think makes it all click. I use a rope when pulling by hand and the metal hitch from Otter when connecting to a sled or wheeler.
2. As far as what size to get, just like the trolling motor on my boat, my truck and many other outdoor items I always tend to go bigger as you can never go smaller to some degree. I fish solo many times and I can still load my Pro Lodge in and out of my 1/2 ton pick up box with no major struggle. I lift one end onto the tailate and then lift and slide the rest in. Sometimes I take the Auger out and put it in after or on the side of the truck box. Long-story short, all the times that I am fishing with another person, I would never sacrifice the extra space and downsize to a cabin.
3. The poles are not going to bend, and make for a great strong frame.
I shall note that there are many “good” portables on the market, however I just feel that the Otter’s are better than the competition. I agree with you on the Ice Camo- however after using mine a few times, I dont even notice it now. It could be bright pink or purple and I would still not care as I know I am going fishing, going to be warm and the afterall the fish don’t have a clue. If you like to have quality possesions and take care of them, then the Otter is the way to go.
Good luck fishing,
Jake