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Alot of questions there!
Do you know what you're planning on taking? 2 up plus cooking and camping equipment is a lot of shit. 100% possible but I'd seriously consider hopping between hotels. Also consider a couple of hammocks if you're going to be camping in wooded areas. If you are set on camping, I'd seriously consider the hobo life - 2-3 days for boxers, 2 for socks, week+ for shirts (smell test everything). Pm me and i can send you some pics of my bike, i can suggest a few ways to eek out more luggage space for free/cheap.
I always try to carry enough water for 2 days on the bike (4l), maybe just 6l with 2. I go to remote places though where you only see a handful of people in a day, if you're on the beaten track it's less important.
Also, riding on trails 2up can be ok but anything other than "smooth" dirt roads won't be a huge amount of fun for either of you. Riding on pavement is obviously much more comfortable but you'll probably find yourself wishing for more HP, particularly at altitude and going up mountains. Though, smooth dirt can be good fun 2up.
300 M per day 2up is a good amount on pavement, its alot for off road. Sometimes i ride a everyday for a week, sometimes a road will ruin you after 2 days and you have to rest. It is a "skill", and does increase quite slowly so for the first couple of weeks you will probably want a rest every 2 days.
My bike has crossed 60cm deep rivers and ridden through torrential rain without any problems, i think it's waterproof enough.
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