I can give replies to most of your questions, but it will take me a little bit of time to do so (and I'm at work right now). Would it be better suited to a PM?
Personally, I would get as much experience around horses as possible between now and then. It will allow you to deal with a horse who does NOT want to cross X stream, to recognize lameness or injury and possibly learn how to treat them, and learn exactly how much horses DO eat (about 2% of their body weight per day at a low-medium activity level - higher if you are asking more of them and/or if they have high metabolisms). You cannot take a horse out for a month and expect to be able to carry enough food for both of you - you will have to schedule regular stops for refueling and/or put grazing days in every couple of days if good quality grazing is available. Otherwise, you will be dealing with hungry, grouchy, weak horses within a week.
p.s. when planning a long trip, it's best to have at least two horses per person - one to ride, one to carry the pack(s). You switch off daily or when you take lunch.
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