I'm looking for recommendations for the best places to stay in Tokyo and Osaka. Also how easy is it getting around? Do I need to buy any kind of transportation passes beforehand?

If you're going to other towns or cities other than that, get a JR pass now (can only be bought outside of Japan). Otherwise, it's not worth it and smart cards like Icoca, Suica and Pasmo can be used in both cities for metro and buses.

You can buy the smart cards at the airport, put whatever amount you want on it and refill anytime you need at the train stations. Just swipe going in and out of the trains or busses. They also accept them at convenience stores. It's easy to get around if you have google map on your phone. I wouldn't try it without that. You can buy your JR train pass voucher at Nippon Travel downtown. I was in and out in less than 10 minutes. I'm pretty sure the regular cost of the train to Osaka and back is more than the JR pass. Plus you can use it on any JR line for day trips. You switch it out for the actual train pass in Japan at one of the stations. I would find a hotel within a few blocks of a train station as you do more than enough walking to start with.

https://m.youtube.com/watch?v=6AXZ-s4TN8c

We stayed here in Osaka and really liked it , close walk to the transit
https://www.newotani.co.jp/en/osaka/

The JR pass was epic. You do have to buy it beforehand, and trade it in at the airport or a major station. I did a lot of intercity travel on mine, but for the sheer ease of being able to breeze through stations with just a wave of the pass at the checkpoint guys, it was priceless. And yes, a bullet train trip from Tokyo to Osaka and back might well be more expensive than the pass, it's worth checking into.
I did have a Pasmo card, I barely used it.
Google Maps was the shiznit in Japan. Anywhere I went it could tell me the transit options. It wasn't always 100% accurate, but it was close enough. I had a pocket wifi so I had Google Maps and internet on demand, best $100 I spent on the whole trip.

Joshua CadrinJosh

Terra who is Joshua cadrin

Josh whoops

Terra Thanks though, there's some good advice here

www.hyperdia.com has all the train and metro updates and a trip planner. And there’s an app.

Easiest transit system. In Tokyo buy your Pasmo pass for transit. JR pass for travelling on the billet trains between cities. If you’re only going to Osaka a JR pass maybe overkill and you may want just one individual ticket.