Anyone who knows even a tiny bit about Japan will know that Osaka and Tokyo are two of the biggest cities here in Japan. Thus, locals and tourists alike have come to compare the two; whether it's about being competitive or simply to choose which destination to visit (due to limited travel time).
I can tell you that I am definitely Team Osaka, if you will.
It probably is extremely bias and subjectively (which it is), as I've only lived in Kansai since I first moved here to Japan. But I had to choose again, I would probably still choose Osaka over Tokyo.
I don't think Tokyo is terrible at all. In fact, I think Tokyo is absolutely superior in many ways.
Despite both being huge metropolises, Tokyo is still more convenient than Osaka. No, I'm not talking about just daily conveniences. For example, some travel destinations are actually much easier to get to from Tokyo because the transport infrastructure is in place for faster travel from Tokyo only, not Osaka. Like going to Kanazawa. Which is something that boggles my mind. No matter how you look at it on the map, Kansai is definitely closer. But Tokyo has the high speed rail that gets there faster.
Or... having to go to the embassy to renew a passport of your home country. You'd most likely have to make a trip to Tokyo in order to at least start this process.
As an expat, having food from your home country becomes much more desired the longer you stay in Japan. Yes, while Japanese food is great, you will eventually start to crave foods from other cultures - especially if you have been exposed to them frequently back home. Tokyo definitely wins in terms of having more available options. While it's not impossible to find some variety in Osaka, the quality of those options are questionable at best. If you read my blog about Cantonese Food, you will understand what I mean.
Tokyo is... huge. Well, that's a bit of an understatement, but what I am trying to get at is that in a huge metropolis like Tokyo, it's often not hard to find lots of events happening and lots of places to explore on your own free time. The former is especially true. If you know where to look, there's always something happening somewhere in some part of the city.
Which the same could be said about Osaka as well. There are plenty of events that happen every weekend that's related to art, food or general entertainment. It's not difficult to find at all if you aren't too picky. However, being Osaka sometimes mean you can miss out on bigger events that is stationery in one city like the Tokyo Game Show, which is only held in Tokyo.
But the amount of people in Japan's biggest metropolis is really the main reason I will still choose Osaka over Tokyo.
The older I got, the less I wanted to be around the glitz, the glam and the people. I mean... I've always been very much an introvert so it's kind of ingrained in me to avoid people. Haha. But I still wanted to be in a place where there were ample job opportunities, places to meet different kinds of people (to avoid people drama... which I still had, so you can only imagine what it's like in a small town).
Having come to Japan via a dispatch company, there is often very little chance for you to choose a placement in or close to a big city. I didn't really bet on getting one at all, but somehow the stars just kind of aligned and Interac had placements in Sakai City (30 mins out of Osaka proper).
I took it and stayed since.
So if you really had to ask me why Osaka, not Tokyo...
I didn't choose Osaka, Osaka chose me.