c) It'd be cool to pop up the nearest road name. Chances are that we should be on it.

Roadmap v1.0rc3 has this ability, along with the ability to display road names, at approaching intersections and even use Flite to text-to-speech them. I'm planning to re-work the "bridge" between GPSApp and Roadmap and integrate version v1.0rc3 of Roadmap sometime reasonably soon. If Jan wants to give me some guidelines for making a "bridge" that would be welcome..
d) Labelling major highways at an appropriate resolution.

Map Labeling would be nice but Roadmap doesn't appear to even do this, maybe the latest version does.. haven't installed it yet.
e) De-cluttering some of the big-scale zooms. It appears as if we still get dots where some of the roads were. Ideally if I go to a 5mile+ scale, all I want to see are major roads.
(Interstates, turnpikes etc)

I think what your seeing mainly here are bodies of water which aren't decluttered by default- you can mess with this in the schema and/or preferences file I believe. Real large scale zoom outs are dangerous anyways because they require so much disk reads that the empeg can easily get cloberred.
f) It'd be nice to shade-fill water. It appears as though it is displaying line data for shorelines already. I'm not sure how feasible this is.

The code for this is probably already in roadmap, I just need to write the function that draws it correctly. I tried to use the function in vfdlib.c that draws polygons filled and it seems like it didn't clip correctly and clobbered the whole screen. Hard for me to test this shoreline stuff though, only body of water I have here is the ole Mississippi..hehe
3) It would be cool to implement a road name search. My brief source code excusion suggests that the underlying data should be there in a searchable form. I don't know if it would be possible to implement a fuzzy search similar to the empeg's song search feature, but that would be ideal.

Roadmap has very nice search functionality.. if you try the actual Roadmap program it works pretty well. No idea how you could put in what address you wanted though on the empeg without the remote or something.