I've been meaning to address the particulars of the Keshlan conflict for some time now IC, but i may as well give you all the information available to Raynor.
Currently, three major factions have established themselves as powers in the Keshlan Isles. The Imperials claim to have various members of the Royal Family in custody, and plan on returning the Dynasty to power. Currently they are entrenched deeply on several of the larger islands, and have managed to repel invasions by the Revolutionary forces by virtue of a strong land military. However, their navies have been thoroughly crushed, and mages are flocking to the banners of each of the other factions.
The strongest faction in the Isles are the revolutionary forces, who plan on establishing a new mage dynasty and drastically overhaul the class system. It's complicated, and Raynor doesn't fully understand it, but Mages are traditionally considered casteless, which disqualifies them from inheritance or from holding any authority or prestige. The Revolutionaries seek to abolish the merchant Caste and replace it with a Mage class.
The third faction has not declared outright hostility with the Imperial faction, but things are tense between them. They call themselves Reformists, and are not averse to the idea of the Imperial's returning to power, so long as various laws are changed. They also want to change the caste system, allowing mages to be a part of their family's cast. Some minor lords who've managed to come away with their holdings intact are declaring alliance with the Reformist faction, under the condition they be allowed independence should they win.
As for Geography? Most of the Keshlan isles are clusters of small islands, but some are quite large. The largest, the seat of the Empire, is roughly two thirds the size of ireland. So yes, while Keshlan power is tied strongly to their navy, and their skilled sea mages, land power does play some part.
Barick's training hasn't involved scoring hits, rather whenever you've made a mistake he's let the sting of his stick serve as the lesson. When you've trained in armor he's mostly just picked up speed and power in training, tiring you out more than anything.