My first tip: hire a pocket wifi! (this is the most convenient thing to have as you travel). You can pick it up in the post office or airport when you arrive in Japan. JR Pass offer this service but there are a couple other places that offer it for different prices (soz i cant rmmb which one i used. but hv a look around)
2nd tip: it depends where you're going, JR Pass tickets can be unnecessary. If you're going via shinkansen a lot, then it'll be cheaper using JRPass but I found that I ended up using the normal train a lot so had to tag on/off with my SUICA/Passmo card (-> train recharge cards that you can refill & buy at the train station).
Going with someone else would be good I reckon. Less hassle for you (esp if they've been there before) hahaha. Good luck and have fun tho! Just enjoy the journey :D
I am planning a trip for japan, but I'm confused by airplane cost and travel expenses. Any one have advice for first time travelers?