Any decent sledding slope would need to be waaaay bigger than what was in Snow Town. Definitely possible though. If on the overworld, development would need to be okay with appropriating a very large amount of space to a very large mountain with a low density in other content such as hat shops. Also, there is only one person I know on Graalians that seems OK with tiling cliffs at all, and he seems to avoid it.
One time, I tried writing software to automate that kind of thing for tiling systems in general (i.e. define a pattern, a direction, and junctions with other patterns). My linear algebra skills simply weren't good enough for my ambitions, and they're weaker now because I haven't practiced them. Junctions are definitely the hardest part because they can be quite arbitrarily defined.