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Hypermotard/strada or Tiger 800?

Yeah, the Hyper is a better-looking bike than the Tiger in my opinion as well. It really does sound like a choice between form and function for you.
Monsters are great for lane-splitting. Hypers and Tigers will have a little tougher of a time with their wider bars as you probably are aware- also Monster handlebars are lower while Hyper & Tiger bars are right at car mirror heighths. Something to consider for sure.