As a fan of Glen Cook's Black Company, I'm super down for this.
However, I'd like to make a proposal. As written, the RP seems to be very small-scale; most companies probably won't exceed 20 or even 10 men. Personally, I'd be more interested in a slightly larger scale; in the realm of controlling small, private armies.
I don't want to derail the initial system, but if other players are also more inclined towards a bigger scale, then I might suggest instead of hiring and equipping single individuals, we replace them with formations of men, and any equipment or upgrades they receive can be treated as unit-wide. The possibility for RPing interaction between key characters can still be there, while players can control companies with a little more substance and bearing on the setting.
Again, if popular opinion leans toward the single-man, small-scale, then I've got no problem with it; but I'd really be more invested in a RP with more bodies where our actions carry more weight.
Examples:
Rather than hiring one warrior with a fine-condition sword, I hire a unit of X warriors with fine-condition gear.
or I upgrade a unit of X scouts to skirmishers, and give the whole unit the Y feat.
The CON/DEX/WIS stats could represent the respective strength of a body of men, rather than a single man.
The HP system could represent casualties in the units, and fighting could still be done in a grid, with letters representing formations. Not much would have to actually change, mechanics-wise.