Planning a trip to Japan

Some super cute stuff I got...



And they shall be my companions to Japan this year!! *AWWWWW* For those who are wondering, I'll be heading to...
SG --> Tokyo --> Kyoto --> Osaka --> Hong Kong --> SG A total of 18 days!! GUESS GUESS GUESS HOW MUCH ARE ALL THE TIX???
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$1000? $800??  Nope to all the above!
It's only $660!!!!! Am I budget barbie or budget barbie lol
So anyway, planning REALLY isn't easy, especially when English is not their first language. It feels like Korea all over again ~.~  Spent almost the entire day today settling the transitions between places to places and HOTELS!! Whoa hotels really giving me a headache. It's SO DIFFICULT to find a really cheap and affordable hotel. I mean.. there are some. But they are soooo out of the way from places in Central Tokyo like Shibuya, Shinjuku.. And then hotels around these area are all so damn ex la!! If you want cheap ones, have but they are hostels or private room with shared bathrooms kind which I don't really like. And I also need hotels with Wifi so that I can BLOG and surf the net/check places of interests/maps. I nearly puked out my eyes today comparing hotels against hotels, checking maps after maps.. Mehh. But thankfully!! The kind people at hotels.com (did a blog event with them before!) gave me a 10% discount of ALL my entire hotel stays which actually helped me saved ALOT. And also luckily as well as thankfully, I have an Aunt in Hongkong so imma just crash at my Aunt's place!! Heee 
So glad I finally settled everything (flights/bus/trains/hotels.. whatever) already. I need this sense of security that I have my journey planned and a roof over my head when I'm there. So now, I have something else that's bothering me.. which is.. DATA PLAN. NEED NEED NEED to have a data plan to whatsapp, instagram, check my emails on the go and just basically, still stay connected to my family&friends in Singapore!! And getting a mobile data plan in Japan can be a headache cuz the telecom service over there have such weird rules like u need to have a one year contract?? There are some others which offers you other data plans packages which comes at an extortion price. So I'm thinking of signing up for a Boingo account so I can tap onto the wifi and this seems like the cheapest alternative!! 
Anyone been to Japan and can help me out with this??? :( And also any other recommended places to go? I will be so grateful! :D

Ending off this post with this picture!
It shall be my motivation to work hard now and enjoy later!!