I like to take alot of crap with me so I am hoping to use my wheeler this year. I have an old otter 2 man and a pop up . The pop up weighs less but the flip is easier to set up by myself especially in the wind. Both are not bad to heat.

Right on. I just can't drag or lift the big flip over very well. They are much more comfortable as is the pop up but I'm kinda mobile. When with friends we just toss up a home base pop up ( killzone) and branch off.
Now it's time to put the tip ups away and break out the silver bullet gear

If a guy was lookin to purchase say.......  a new ice fishing hut and this guy fishes mostly by one's self and must manually drag his equipment because his stupid state disallows any motorized vehicles on the ice.  What one hut would be the most likely recommended, keeping in mind the hut must be transported and set up by one little old guy unless, a couple of his friends convince him to take them fishing.  Therefore the hut should comfortably seat no less than two people, plus gear, at any given time?  Also keep in mind, these friends couldn't stack bales of hay in broad daylight on a mild summer day so absolutely no setup/tear down help can be expected.
 
I'll be researching ice huts on FishUSA for a bit, so please feel free to leave a suggestion or two but it keep it quiet as I think the wife may be listening.

BeenThereDoneThat.
If a guy was lookin to purchase say.......  a new ice fishing hut and this guy fishes mostly by one's self and must manually drag his equipment because his stupid state disallows any motorized vehicles on the ice.  What one hut would be the most likely recommended, keeping in mind the hut must be transported and set up by one little old guy unless, a couple of his friends convince him to take them fishing.  Therefore the hut should comfortably seat no less than two people, plus gear, at any given time?  Also keep in mind, these friends couldn't stack bales of hay in broad daylight on a mild summer day so absolutely no setup/tear down help can be expected.
 
I'll be researching ice huts on FishUSA for a bit, so please feel free to leave a suggestion or two but it keep it quiet as I think the wife may be listening.

If going with another, I'd recommend a hub shelter. Cant give a specific product due to mine (killzone) is no longer available . I'm pretty sure all the other manufactures are reliable . I spent $99.00 on the smaller zone and $150.0 on the larger.  Larger is better, to a point.
Tips : would be height. My smaller 2-3 man hub is a 2 person shelter and standing up means hunching over.
The larger 3-4 man is a good 3 person that we can stand up straight. Personally, I'd keep my price in that range , give or take.
Any hub (pop up) pretty much requires 2 to set it up, especially in wind although I've done mine solo.
Mine have a single 2 zipper triangle door. 1 zipper means 1, less thing to malfunction. 2 doors are not necessary.
 
These days I rock my shappell rover (no longer available ) or the Shappell 1.0, an excellent shanty.
No way it will fit 2 people but its a great all in 1 sled @ $249.00 which has remained stable price .
I'm very mobile with that sled solo. 
 
 

Thanks HT, height is important when it comes to being comfortable.  Being able to stand and stretch while staying inside does make for a more pleasant long term experience.  I suppose two doors would be better if interior room is limited, just to make moving in and out a bit easier on the occupants. 
 
I was just looking at and watching videos of the ESKIMO 3 and it doesn't seem much different than setting up/tearing down a hub style ground blind except I'll be damed if I can ever get that blind back in the bag.  I'm looking at the non-insulated that only weighs 18 pounds.  I have a 30 year old 2-man hut that's not insulated so I don't think that would be a big issue, probably just as clumsy to set up and weighs 40 pounds and it folds up into a suitcase style base that measures 2 foot by 4 foot.  Mice have put a few extra ventilation holes in the walls over the years but the Gorilla Tape is holding up well, even in sub-zero temps.
 
Got a nice FishUSA gift card for Christmas and ya know how those dam things can burn a hole in your pocket and seeing hows the ice is upon us, wellll the rest is history.  I know we don't get the ice like yinz mupp north but it sure looks like we're getting some ice fishing time this year.
 
Thanks again for your advice and may the new year bring you and yours good times and tight lines.

I have a hub like this and I can set it by myself if it is not too windy.
http://stores.clamoutdoors.com/clam/shelters/vista-link-6-x-6-hub-2-3-anglers.html
I ask have an older otter flip 2man I got for free, just had to patch it up from mice holes. Does not look pretty, but it functions perfectly. It is heavier, but more mobile and a snap to set up. Both will fish 2. Rule of thumb on hub style  is to take the number of people they say and take away one and that what it will fish comfortably. 

My eskimo quickfish 2i is about what you need john. Small enough that its easy to transport and pull and sets up quick and easy. Just get a decent drill and adapter for the ice stakes. If windy put 1 or 2 in before you set up to make it alot easier. It was -3 when i set up and with my lantern and little buddy going my coat was off all morning.

outasync
My eskimo quickfish 2i is about what you need john. Small enough that its easy to transport and pull and sets up quick and easy. Just get a decent drill and adapter for the ice stakes. If windy put 1 or 2 in before you set up to make it alot easier. It was -3 when i set up and with my lantern and little buddy going my coat was off all morning.

I'm liking the looks of the Eskimo 3 but not sure of the insulated as that about doubles the weight. Was wondering about the need for a drill motor to install and remove the anchors.

I was comfortable in my hub today at -3 .  I would say my heater kept it in the high 40s maybe 50 I would  guess. Comfortable with no hat or gloves, but kept my coat on.  It also frosted on the ceiling and rained on me too.  An insulated hub would have been much warmer. Just depends on how cold you go out in and how warm you want to be.  A drill is a must to put the anchors in.

Right now I am looking at -2.5F. with just a hint of a breeze. Fortunately I'm 'snug as a bug in a rug' sitting in my living room counting the minutes till I light up the new year sky. However, the weather dude is saying to expect more of the same through the coming week and I doubt any new fishing shack will arrive in the very near future. So it looks like any ice sitting will need be done in my trusty 30 year old 2 man uninsulated duct taped shanty (no standing). I can keep warm using a single mantle lantern but do have a propane radiant heater on standby.

Clint I remember a few times, over the years, getting rained on inside the shack. Them was some cold days on the ice, for sure. Thanks for the memories.

Having spoken with Outasync, I shall eagerly await (hopefully in the near future) FishUSA putting the Eskimo 3 on sale.

Gotta git, just enough time to lock and load the launch tubes.

May the new year bring all; good times and tight lines