Your location is indicated as Singapore and driving in Singapore is on left side so that should help. Definitely if you can read Japanese then that is big plus since you will able to read road signs.

I do not know about roads in Singapore but comparing with typical driving in the U.S., roads in metropolitan Tokyo area are very narrow. A road which would be a single lane one way road in the U.S. would easily being used as two way roads with oncoming traffic in Tokyo. When I started to drive in Japan I found that driving outside of Tokyo to be easier, because roads can be wider and there are far less traffic on the road.

Yes, while maneuvering such narrow road when there is oncoming traffic, I have to be careful with bicycles on the side of the road. When I started to drive in Japan (in metropolitan Tokyo area) I really thought I will hit few people on bicycles. (Thankfully I did not end up hitting any people on bicycles. )

I think form my experience, driving in downtown Boston come close because downtown Boston was built and designed before automobile where small wagons were norm on the road.

For me it was change from driving on right side of the road to left side of the road. That also means change from sitting on left side of the car for driving to sitting on right side of the car for driving. Even if you can drive manual transmission this involves change from shifting using right hand to shifting using left hand. It sure took me a lot to get used to, not recommended driving manual transmission in Japan if you are used in shifting using right hand.

Also, sitting in right side of the car for driving, driving reverse was very weird felling for me. In the U.S. sitting in left side of the car then I turn myself to right to see the back while in reverse. But in Japan sitting in right side of the car then I turn myself to left to see the back while reversing, that really was weird feeling for me when I started to drive in Japan.