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I've only been to Toledo once, so I can't comment too much, but I would generally say that the two are very much alike- both are rust-belt, blue collar cities located at opposite ends of Lake Erie (and have the associated recreational benefits of being on a big lake). Both have declining populations and are shells of what they once were. Buffalo has almost certainly fallen harder than Toledo and continues to do so. However, Buffalo is more "well-known" to out-of-towners, usually due to weather or sports.
In each of those categories (skyline, food, culture, downtown, attraction), I think Buffalo wins easily. Despite having a smaller city population, Buffalo has a larger metro population and simply has a bigger-city feel than Toledo. I was only in Toledo once, but it was a Friday night and the downtown area just seemed dead to me (not that Buffalo is incredibly vibrant, but at least some stuff happens on weekends in downtown Buffalo).
Buffalo is a much larger msa (approximately 1.1 million vs 650,000 for Toledo) and was historically much larger than Toledo so it is tough to compare in terms of skyline, culture, etc. However, most people are surprised at the quality of restaurants that are in Toledo, as well as its art museum and zoo!
To be honest, a Toledo vs. Syracuse comparison makes more sense.
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