Won't there always be that certain point? At some point you have the best items and the highest lvl. There is nothing that can be done about that. Adding more items/lvls only works up to a point, because too high item stats (things like speed and damage) break the warband combat system. Too high stats result in things like attacks being faster than the animation plays, in other words invisible attacks, arrows firing from bows before the archer has drawn the cord, that sort of thing.
There might be a certain maximum point in theory, but with appropriate design even the most hardcore players can continue making real gains - slower and slower though it may be - without hitting that limit almost indefinitely. Where the game engine demands limitations, let there be stat allocation limitations if need be; e.g. make 200 wpf or whatever number the max. If attaining a higher level resulted in having excess wpp beyond that, there's always putting points into a different weapon.
Given the current game design, there's really no reason in these terms why the level cap couldn't be considerably higher. Even if limits need to be set on whatever stats to prevent 'game-breaking' situations, there is more than enough room for players to expand with multiple skill specializations. Iron flesh, athletics, shield, power throw, riding... lots of ways to expand a build if you could go further than is currently possible.
But what seems the silliest to me is how quickly you reach the top now. Okay, sure, if you forgo retirement you could eventually go up.. a few more levels. Or with retirements, you can get some small bonuses from heirlooming stuff. Still, consider how quickly I can purchase and use (though not -all- the time, with repair costs) the best equipment - the most expensive at least - as opposed to how very long it takes to get the relatively small bonuses from heirlooming: Let's say that the average bonus multiplier is 2x, so you're earning 100 gold and 2000 xp per minute on average. (Slighter less with repair costs, but I'll ignore that.) So in.. under 6 hours, I can earn enough gold to buy Black Armor, with 60 points of body armor. But reaching retirement, so I get heirloom that armor for a few more armor points.. that's something like 73 hours of total play time.
If it were me designing the system of play from the ground up, I would make it take much longer for a player to get this top-of-the-line type equipment. Granted, you want a curve of reward that is somewhat faster at the beginning, and after some point the progress must become much slower. But if you can get to within 90-95% of the max in a few weeks of playing.. that just isn't a curve designed for longevity.
Now.. better diversity of game features is more important than all of that. Not that there is any reason why there shouldn't
also be a well-considered achievement curve, in addition to more game modes, Strategus, etc. But these issues seem especially significant now, given the general lack of new game features over the past however many months. Hopefully there will be some remedy on that front some time in the not too distant future, but as of now, when there's little else to do but fight, fight, and fight again while leveling up.. the unnecessary inelegance of the leveling/equipment system become more and more painful.