I've been to Japan a few times before on business, but I've always flown into a TYO airport. I'm planning an upcoming tourism trip where my first night is in Osaka and my last night is Tokyo. My current flight lands at HND around 3:30 PM and I just planned on hopping on a Nozomi train once I got to Shinagawa station from HND. Is it worth considering flying from HND to ITM? The earliest flight I'd feel comfortable booking is ~5:30 PM. I think this puts me at my hotel in Osaka at roughly ~8:00 PM which is pretty much the same time I'd expect to get to the hotel if I used the Shinkansen.

Anyone have suggestions? The difference in price is negligible for me since I'm looking at green car with cash or 787 J with points.

Flying into KIX doesn't really work for me.