I'm a fan of optional and other algebraic datatypes, you don't need to convince me. It's in our roadmap doc! :-) OTOH, Swift has way too much special purpose sugar which I'd prefer to reduce this time around, there are ways to have the best of both worlds - ergonomic and extensible.
Remaining faithful to Python's syntax should certainly help avoid too much special purpose sugar. Most Python enthusiasts seem to be on low sugar diets.