I've been through something similar with a static caravan setup, and the shepherd's hut is honestly the perfect starting point — you're working with limited space, which forces you to be disciplined about loads.
The winter shadow thing @VanGill mentions is spot on for your area. I'd add: walk the site at solar noon in December. Literally stand where your panels would go and watch the shadows move. You'll see things a site survey might miss.
What actually made the difference for me was front-loading the load audit. Before touching a single panel or battery, I spent three weeks documenting what actually runs and when. That emergency backup mindset helps — you stop dreaming about powering everything and start being ruthlessly honest about what you need to function in January.
The shepherd's hut's small enough that you could realistically run on a modest Victron Multiplus setup with 10-15kWh of storage. Start there rather than overbuilding. You can always expand the solar array, but oversized batteries just sit there eating money on maintenance.
What's your heating situation looking like? That's often where people underestimate winter demand.