If players were evenly split in all 3 major cities, there would be more room to place retainers. The problem's still there though. XIV's player base is incredibly small. The people who designed the MW system must have forgotten about limitations unless they knew their player base would remain ridiculously small, and that's negative thinking early on in development and I'm guessing the true story is they didn't think it through.

Away with the MW system, it's EXACTLY what the auction house in FFXI is, except it adds unnecessary and complicated steps to what can easily be accomplished via a simple UI menu.