I'm not speaking for myself here because I'm on a fairly low pop server and got exactly the houses I wanted without competition both times I tried: Large house on plot 46 for my FC when Shirogane first opened and medium house for myself on plot 31 in LB when they added new housing.

That being said, I know this is a problem on high pop servers. I have friends who tell me about plaquard spamming and how awful it is. However, after adding new wards MOST servers have an excess of unclaimed cottages. So, from SE's perspective, the housing market is balanced now. I know you're thinking 'but I'm on a high pop server, they should give us more housing.'

Have you ever considered this terrible housing situation may be intentional? Think of it from SE's perspective: they DO NOT want you to be on a high pop server, period. SE wants their servers to be as balanced as possible, so they offer incentives, such as free Transfers to low pop servers, road to 60 buffs, sometimes they won't allow new characters to be created on legacy servers at all. High pop servers are causing some kind of problem, so they are trying to incentivize people to spread out. Adding extra housing to high pop servers would do the opposite. It would incentivize people to stay on those servers, not make them spread out. In fact, the housing situation is probably the best incentive they have to force people to spread.

And I'm sure next time they add wards because the market becomes unbalanced or they add Ishgard housing they'll add the same amount of wards on each server and it won't be enough for high-pop servers. Purposefully. Because you're not supposed to be on a high pop server in the first place.