The greatest challenge I face in winter in a tiny house is the lack of a hall way. A place to leave dirty shoes on a rug, a place where I could take off my shoes when I come in. A hall way would also allow me to preserve the temperature in the house, because right now, when I open the house door, the temperature exchange with the outside is huge. Which is neither practical, economical, nor ecological.
Also a hall way would be the place where I would leave my shoes warm. Not outside in the rain or freezing cold? Who likes to put on wet or cold shoes?
Another challenge when the summer days are over is the water. Why? Well, The rain is simply pouring down the outside panelling and on to the door and windows. This is bad juju for the wood all in all.
Recently I had to fix a 1 year old door, because after the second towing of the tiny house for a distance of only 100 meters, the door corner came out of its place and a beautiful crack showed up. Well, the pouring rain was finding its way inside trough that crack.
I personally find it impossible to keep clean, a house that has no hall way, no place to dry your wet clothes or hang clothes you have washed.
Would I give up the tiny house in winter? Kind of yes.