Just on the stroller aspect, maybe consider a very small, cheap umbrella stroller instead of a bigger stroller you might currently use. While the notion the your older kid might benefit from standing on the platform and being pushed around seems nice a larger stroller means more effort for you guys and it makes navigating the crowds much more difficult. I'd recommend as small and maneuverable as possible. When we had young kids we had a typical big ass stroller for the city (ie. zoo, mall, grocery store, parks, etc) and an umbrella stroller for traveling and using in crowded situations like at the Stampede Grounds or Lilac Festival, etc.
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