I've made four photographic trips to Cuba- in aggregate more than a month. I don't believe I've ever shot a landscape. Cuba is a place to go to photograph buildings or people or cars. The countryside is frankly not terribly interesting The only thing I'd say about either of the outfits you can choose is that you have nothing beyond a std lens in either, and that would affect me. Personally I'd take an slr and one short and one medium zoom to minimise lens changing and get me good framing on the street.
Two systems? well I rarely go on a trip without back-up, which may stay locked in my hotel rooms for the entire trip. But as a person who has had a couple of trips badly affected by camera malfunction I find it pays to prepare for the worst. Certainly given all the complexities of organising a trip to Cuba, the idea of settling for a weeks tourism with no camera simply does not compute. Other people may have different motivations but for me, if my only camera broke I'd want to get right back to the airport rather than deal with the frustration of not photographing.