As I understand it, the server DynMaps (which, as an aside, might be nice to have easily accessible from the website here) used to be much bigger, but were scaled back to just the area around the spawn because of the huge data demands they had on the server. I'd like to propose a middle ground between the options, which is to make it so the Dynmap is extended out to the area where new players are deposited via the WilderWarp (so ~3000 out from 0,0 or so).

Why will players enjoy this idea?
While players can of course make their own maps of their immediate surroundings in-game, the DynMap definitely helps give the world a connected feeling, and allows people to see the server grow as well as identify good spots to build.

How does this idea help or enhance the values of WilderCraft? (Kindness and cooperation, hard survival gameplay has costs, power has trade-offs)
A DynMap display of the area where most new players will be starting off would definitely be a boon on their behalf. Advanced players frequently move further out into the world for either privacy or specific real estate demands, so the limited range of the DynMap wouldn't be 'spoiling' the locations of such.

On a scale of 1-10 (1=easy, 10=hard/complex) how complex is this idea?
I'm not personally familiar on the specific mechanics of DynMap, but depending on how much of a toll it takes on the server it could be as simple as changing one or two data values. So I'd perhaps rate the complexity between1-3 depending on what it'd do to server performance.

It's just a disk-space issue and last season we ran out quickly. This season I've upgraded the hardware (thanks donors!) so we should be able to do this soon. I'll run some tests and see how it goes.