Even though you initially stated you don't want free stuff and unterstand the workings of grind in MMOs, and considering you contradict yourself there by arguing for a more lenient approach and less timesink, bear with me:
If that (the above) however is no option for you, for whatever reason that might be, you should not expect to be handed what others have gained by playing together, by running an 'organized' (note: I am using this word extremly lenient, as just about any kind of organization will quadruple the returns of whatever you desire to get in this game) group or guild.
Note that these very guilds and groups putting effort and time into the game are the very same people that keep this server populated and the fights going (especially as they will not engage in fairweather play), its their fair share of perceived progression, reward and rightful claim to not have gear dished out en mass to everyone.
Now let alone the carrot-and-stick thats ultimately required to incentivise players to stick around (and to keep altoholics in check *cough*):
In regards to 'population' (by extension RvR system): There will always be a core of players that don't care about gear; that play 'just for the sake of having fun', and ultimately are - by default basically - decked out on everything as they have unterstood the very dynamic of this game; the population will heavily fluctate.
It is a private server for a dead (niche) game, after all ~ expecting it to gain traction, or maintain a steady population if things are flung around for free and if efforts of the communtiy aren't rewarded (if not even indirectly tarnished a tad) is adorable, but its not feasible.
People that don't stick around with the current 'grind' in place, will not stick around either way - every new release will chip away at the population, depending on the nature of these releases it'll either be temporary or permanent.
No approach to handling gear distribution will change that; the issue with population will always persist in a way - funneling people into one zone and having the flip take that long is therefor (and due to tech limitations, lack of feasible concepts and development time [devs are running on fumes, given that they have an actual RL to manage aswell]) necessary, its not the optimum and will surely be changed in the future, but its certainly not one of the priorities and won't be for a long time I figure.
Last but not least there is basic psychology - even the most die-tryhard WAR players, those most addicted to it (e.g.: myself), will lose interest if theres nothing left that allows their brains to drown in dopamine.
As harder and longer you 'work' for something, for example not only gear but your character in general; min/max (RR) and such, as more fun stuff happens in your brain once you get what you've 'worked' for - as more improvements you can perceive as merrier.
Even more importantly: As more time you invest into your character; into the game, as harder it becomes for you to ditch the game, the time investment is lingering - so are your brain's expectations in regards to it's daily dose of dopamine (if you ever worked for anything related to rehab or alike, you'll get the hint).
The latter is what the RoR staff tries to abide by, for good reason - there have several dissertations and scientific papers been written about the deployment of psychological measures, workings and necessities in and of MMOs; games in general, and that not just for the fun of it. Take World of Warcraft as an example, why do you think it is such a success and more importantly why do you think it still has a very strong population (for its age it is impressive, especially out of a certain perspective...)? Hint: Its not because its a perfect or a remotely forgiving game in terms of time spent.
As to the economic argument: It doesn't apply. You can substitute the economic drive with the nature of this game, i.e.: PvP and the far more severe dependence on population and you, once again, are forced to deploy these measures to keep things afloat - if you don't, well, again...new releases have an ever higher chance of permanently chipping away at the population, as there is nothing you would think twice about ditching or revisiting if you had not invested <alot> of time into it ~ social contacts and shortterm fun (= the kind of fun you can have whilst pugging 24/7) doesn't do the trick, for that the time we live in is too fast paced and too riddled with issues; our lives are too riddled with hardships and responsibilities that require conscious decisions and assessment (compared to when, well, we were younger and the first MMO's; games in general, hit the market).
Playing one's subsconciousness is so much, much more efficient in regards to keeping things afloat, regardlesss of the aspect of life that is concerned...
Now, the following might be strechting the limits a tad and will have me sound like a broken record - I apologize in advance if it is a bit too upfront:
Masking this kind of wishful thinking by stating undying arguments, and arguments that do not necessarily pertain to the very essence of your thread (= that are accounted for by tech development, things that cannot be changed by staff [e.g.: population, by extension RvR system], or things that can be circumvented by means readily accessible to you [e.g.: grouping to grind meds to skip lootroll dependence, premades to grind out emblems via pugfarm]) - especially if you don't take your time to see whether what you are about to type out has already been flung around a million times, and subsequently addressed a million times - is rather insulting (even if it isn't your intention to rile people up; I don't mean to accuse you of ill intent),
if not at last to yourself as you quite literally waste the little time you have to play the game with something that gets you nothing but flak and platitudes flung your way.
Hence my suggestion to you to work out something more elaborate to make it worthwhile ~ who knows, you could convince the RoR staff to be a bit more lenient on the grindy side of things if you compiled just enough statements from community members and arguments in a comprehensive manner... or well, you could learn in the very same process about the issue and come to the conclusion that it isn't a thing worth having headaches over, or learn ways to completly circumvent the issues you are having in the first place.
Again, I completly unterstand where you are coming from - I, too, struggle to find time to actually play the game.
