I would expect that within EEA most of the regulations would be the same and I don't think it's the problem.
What you would need though is translated manuals and such by law. Maybe even localized support for warranties that could raise costs to enter a market.
This is only my assumption, but it would make sense, that's why they cover even smaller English speaking countries like Ireland. Or for example Germany is a big market, but they cover Austria too, because they have German language for free.
"they'd have to be a person I'd spend time with when I'm bored" - I don't think this is fair to expect from anybody. It has a similar vibe as expecting from a relationship to pull you out of sadness. You have to be able to enjoy yourself and your time, if you can share that with anybody and elevate it, that's just an extra.
I don't think the Venu line is "smarter" than the others. It's more every day watch design and has an AMOLED touch screen, but the functionality is nearly the same.