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Answering some of these questions.. will go into more detail if you want.
-training (how much is required? im by no means any better than an amatuer)
Some people pick up on riding horses very quickly. Some don't. You need to at least take riding lessons, and include trail riding in those lessons as well. If you can afford it, lease a horse - that way you'll get the grooming/healthcare/groundwork training along with riding.
-food (for me and the horse - what do i need?)
Take food that packages and stores well, and travel as light as possible. You will need at least two horses to one person (one as a pack horse, the other to ride, and you switch off regularly) to carry the weight of food required for even a week. You'll need grain for the horses, and hay cubes if you have enough room/if there isn't enough grazing for them. Take at least a few hours off every day for grazing, and try to camp somewhere where there is adequate grass for the horses and either hobble them or put them out on lines so they can graze. Horses need about 2% of their bodyweight per day in food (so about 20 lbs for an average 1000 lb horse), and they can only carry about 15% of their bodyweight comfortably, so plan accordingly. People food should be dried or canned whenever possible, though cans can be heavy.
-things to look out for- injuries to the horse/me etc.
You'll need to keep a close eye on your horses' feet. They can get stone bruises bad enough to make them totally lame, not to mention splits and chunks taken off. If you can, invest in boots for the horses for really rough terrain - shoes can be slippery and dangerous at times, but boots are removable and will protect their feet over very rocky areas.
-length of time i should do this (ive got a month in my head for now)
I'd go with less than a month if you don't want to take breaks. If you want to go for a month, I'd go a week or two and then camp in the same spot with good grazing for at least a few days. If you can, keep your riding to a maximum of 4 hours per day and keep your speed low. If you want to gallop, do so - but cut out a significant portion of the rest of your riding for that day. Some horses may not be able to go more than a couple of hours depending on their previous conditioning, so you need to keep that in mind. Ideally, you would lease horses for the purpose of this ride and condition them/get to know them over the months before you go. You don't want to discover that a horse you rented is headshy when you're trying to catch them on a mountain.
-season (obviously it cant be winter season in those areas)
Preferably spring, when the grass is relatively young. That way they can eat a smaller volume of grass but still get decent nutrition.
-political atmosphere - central asia doesnt have the best record for political stability
You'll know much better than me on this. I'd avoid anywhere where you'd find nomads with horses, because if you piss them off they may try to steal yours, since horses are very valuable and a symbol of status. Either that or have an armed guide.
-group size - what do you recommend for group size?
Anywhere from 4-6 to 20 horses. Any more gets unmanageable, any fewer gets dangerous because there's less of a herd mentality.
I know of a few people who have done horseback trecks over long periods of time across the US, but I don't know much about other continents, really, when it comes to choosing a place to do this and figuring out the logistics of it. You'll probably be best off picking a country to visit, then looking for companies who offer horse tours or something like that.
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