Where to Stay (Part 1)
When I was there quite a few years ago, I made the conscious decision to make Osaka a base for my traveling. That is, we would travel from our hotel in Osaka every morning, and return every evening. We even went as far as Himeji (姫路), which was almost 4 hours away by train. Part of the reason was to avoid the hassle of having to lug our suitcases every time we changed hotels - autumn clothing was heavy as we were not used to the cold, being tropical country citizens. Another reason was that Kyoto - where we spent a major part of our days on - was only an hour's ride away from Osaka JR train station.
Finally the most compelling reason was that the Super Hotel we were staying in had discounts if you stayed there for more than 7 days consecutively, there was a 10% discount. On average, we only paid 4,000 yen per person - a pretty good deal considering each room came with its own restroom / bathroom, and breakfast! The current offer seems to be a 1,000 yen discount for a 3 night consecutive stay. Sadly, I booked the hotel quite late - about a month before our departure date - and hotels near Osaka / Umeda JR train station were fully booked. We had to stay about one to two train stops away.
Based on this past experience, I am almost certain I would be choosing a hotel next or close to Osaka / Umeda JR train station. This is because (1) there is a direct train from the KIX airport to this train station via the JR Kansai Airport Rapid Service or limousine bus, (2) as mentioned above, it's a hub for traveling to Kyoto and other nearby places like Nara or Kobe and (3) with kids / toddlers in tow, it's almost unthinkable to be changing hotels carrying all that baggage.
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