Osaka, where to stay?

We're spending 4 nights in Osaka and I'm a bit undecided about whether it would be better to stay near Shin-Osaka or Kita (around Umeda station). We've ruled out Namba since the other two are more conducive to early morning shinkansen departures (we'll have JR passes).

We'll be leaving early for a day trip to visit Himeji/Shosha/Kobe, and want an early start when we move forward to Hakone.

Our general itinerary looks like (and no, we're not including Mount Koya):

Day 1 (arrival at Shin-Osaka around 6pm)
- Dotonburi

Day 2
- USJ
- Takoyaki "Museum"

Day 3
- Momofuku Ramen
- Osaka Castle and Park
- Naniwa Kuishinbo Yokocho
- Osaka Aquarium Kaiyukan
- Tempozan Harbour Village and Ferris Wheel

Day 4
- Early start, Himeji

Day 5
- Early start, Hakone

I'm currently leaning more towards Kita... is it a lot more lively (people walking around in the evening) than Shin-Osaka? There's probably plenty of restaurants in both areas. What other things might I want to consider?

I would do Kita/Umeda over Shin-Osaka. When I stayed in Shin-Osaka, it was very very quiet. I don't really remember there being a lot of restaurants since it felt very much like where someone stayed overnight after taking a late train or needing to take an early train the next morning.

Umeda/Kita is also better for when you visit USJ. You'll have two transfers instead of 3. (There are technically direct trains from Osaka Station to Universal Station, but they are not terribly often, you're much more likely to need to transfer at Nishikujo.) And personally, while you can take the shinkansen to Shin-Kobe, usually when people think of Kobe they think of the areas around Sannomiya and Kobe stations which are both on the regular JR line. You can also take the Hankyu line from Umeda to Sannomiya. Hyperdia claims taking the Special Rapid from Shin-Osaka to Sannomiya is faster than taking the shinkansen to Shin-Kobe, though the fastest is if you are traveling when a Hakuto is leaving for Tottori (which will also stop at Osaka before arriving at Sannomiya,)

Umeda

Thanks for the detailed reply rkold.

We're actually heading straight to Himeji from Osaka so that portion will be shinkansen for sure, with Kobe being on the return track. Our interest in Kobe lies in Mount Maya, which is actually closer to bus to from Shin-Kobe so coming from Himeji to Shin-Kobe seems to be the best.

However, our dinner plans are in Sannomiya and I hadn't thought to check the regular JR line out of Sannomiya on the way back to Umeda. That will definitely save us some time, thanks!

It depends where your hotel is located in umeda area . If you don't want to waste time walking to Osaka(Umeda) station from your hotel and gets stacked with people in rush hours, I would recommend you to stay in Shin Osaka and take a Shinkansen straight to Himeji.
It's just one stop by JR between Shin Osaka and Osaka (Umeda). Just a few minutes ride and comes ever 5 or 10 min.
Even if you stay in Shin Osaka, you can come to umeda easily and enjoy restaurants and shopping there.

Enjoy Himeji and Kobe !

I have stayed a number of times close to Shin-Osaka as our companies HQ is there. But the are is very quiet in the evening. The only restaurants are really those inside the station (1or 2 levels below the Shinkansen entry).

So it depends if you prefer to stay in a location convenient for your two early morning Shinkansen rides or more in a "real" part of Osaka. Both are valid options.

Enjoy your trip to Japan!

With Hakone (or Odawarra really) being two hours away from Shin-Osaka, and you are only doing Hakone as a day trip, I would stay near Shin-Osaka. Better the other days have 5-10 minutes added to said commutes than the longer Hakone day trip day.