Visiting Tokyo and Manila and then Taipei layover as a female traveler

Hello! I am on my 30s and thinking of visiting family in Manila in November. I haven't been home for 8 long years. I am from Canada.

My plan is to go to Tokyo first, spend 5 days there (but 2 would be travel time so really just 3 full days), and then Manila for the next 2.5 weeks. And then I have seen a cheap flight back to Canada with an 18 hour layover to Taipei. I thought I'd take that as an opportunity to do a layover tour.

I have never travelled by myself for this far and long, I've always been with family. So while I am excited, I also have lots of thoughts about this. I know I wanted to try solo travelling and thought visiting a city that's known to be safe (Tokyo, but I've visited last year with my sister), a city I don't have issues with language (Manila), and a popular layover city (Taipei) would be good for my first solo adventure.

Another thing I'm concerned about are my luggages. I am sure I'll have 2 check ins, 1 carry on and a backpack. I will be using the airport limousine in Tokyo to my hotel and back so I think that should be fine. Then in Manila it's easy enough to book a ride. But for Taipei, will I have to pick up my luggages for that long of a layover? I'm hoping no so I don't have to drag them.

I dont really know the purpose of this post lol but I guess just to share my plans, and see if people has thoughts or advise for someone like me going on their first solo adventure.

Thanks for reading. :)