28 Jan 2017 - 12 Feb 2017 Plan

Greetings everyone. I have been replying other posts and this is the first question post I'm creating so I'm unsure if you think I left out anything important to assist you in helping me research. Do not hesitate to let me know what other information you need, I'll try my best to provide them. Due to the stated date above, it's a slight peak period on my end and in Japan as well.

I'll be landing in Osaka, ITM on the 28th evening and staying 2 nights in Osaka. Will have a half day exploration before heading to Kyoto to crash over at my friend's place for the night on the 30th. After that, I'll head over to Nagoya for unagi or directly head over to Tateyama to spend the 31st night there if I can catch a bus to Shirakawago.
On the 1st Feb, I'll be heading to Yokohama for 2 nights. Will be heading out first thing in the morning on the 3rd Feb and stay over for a night in Tokyo. Subsequently, half day in Tokyo on the 4th before departing for Hakodate.
2 nights in Hakodate, I'm not sure what to do exactly, since I had been to Hakodate in April 2016. I could have missed out some stuff and I need to relook into that again.
6th Feb, I will be heading out to Furano and check out on the 9th Feb. I will be there for snowboarding and I need help in getting some information on that because it's my first time experiencing snow. It would be nice if someone could research for me what to do to rent the equipment.
I will leave Furano on the 9th and head out to Sapporo for the snow festival event. That's the last on my list. Revisit Otaru because of my previous hectic schedule due to wet weather.

I am fully aware that I'm traveling a lot which is why I'm here seeking help for alternatives in transport cost. Should I get the Japan rail pass or JR Hokkaido pass? There might be other transport cost involved while transferring, hence, I seek your experience and knowledge to help me out in my expenses.

You didn't say if you're flying or catching the train to Hakodate, but if you had a 7 day JR pass you could use it from the 31st til the 6th, obviously catching the shinkansen to Hakodate. You'd only need to pay for the train back from Furano, trip to Otaru and to the airport (you didn't say where you're flying out from but I would imagine that flying there from Sapporo is the best option). I'm pretty sure the JR Hokkaido pass is only worthwhile with long distance travel.

You could always just spend 1 night in Hakodate and then another night in somewhere like Noboribetsu Onsen, Lake Toya, etc. Perfect weather for onsen!

Thanks Sal for your feedback.

I will be traveling just by train throughout this whole journey and a little by bus for some attraction points. The only planes I'm taking is from NRT to Osaka airports (fly in) and CTS to HND followed by a bus transfer to NRT (fly out).

My main concern is traveling to different cities by train only and how much it'll cost in total compared to having a JR nationwide pass and the new JR East-South Hokkaido pass. Should I get a 7 day or 14 day pass, flexi pass. Tokyo has unlimited rides on their subway lines for a day or two at a fixed price for their pass.

I'll be passing through Tohoku region since I had no intention to stop over there unless there's something available there that can make it a day trip while on the way to Hakodate. I have already been to Noboribetsu and Lake Toya so I reckon I could leave them out and try others.