Questions about travelling to Japan

Hi Daniel-san, I'm going to Japan in a few days with my cousin from 12-20 January. We haven't book any hotel for stay because want to search a hotel near train station (somehow it's quite difficult to find).

This is our itinerary looks like:
12 Arrive at Haneda Airport, Heading to Tokyo, Asakusa Sensoji Temple, Nakamise-Dori, Tokyo Skytree, Tokyo Tower
13 Harajuku, Omotesando, Shinjuku, Shibuya
14 Disneyland
15 Fuji Kawaguchiko, Oshino hakkai, Gotemba Premium Outlet
16 Osaka, Osaka Castle, Dotonbori, Glico Sign
17 Universal Studio Japan
18 Kyoto Fushimi-Inari, Gion District then back to Tokyo
19 Hanging around Tokyo
20 Back to home via Narita Airport

So, here are my questions:
1. Can you give us some recommendation about hotel?
2. Do you mind check our itinerary, maybe you can tell us whether we should buy JR PASS or not.
3. Sorry if I got it wrong but as far as I know JR PASS can't be used to Gotemba Premium Outlet right? Can we go there by bus or train from Mt. Fuji?
4. Can I bring any suitcase with me on train or bus?
5. Can I use JR PASS from Tokyo to Osaka?