Pretty Mappoint Maps - NY-29 Party Registration by County
Ok, I know this is a simple case, but just wanted to try something low-key to start out with. Mappoint has some serious limitations in terms of showing and mapping data to congressional districts (or any districts that don’t make sense, which is pretty much all of NY’s EXTREMELY gerrymandered electoral districts). From what I’ve seen, Google Maps has similar limitations, though, so any leads on better mapping software that can handle that sort of thing would be appreciated!
But I can graph data by county, so here’s one on party registration by county for the 29th. Note the effect of gerrymandering to give even Monroe County’s contribution (Monroe has a lot more Dems than Republicans) to the 29th a Republican edge.
Democratic 
Republican
And here’s the party breakdown, weighted for population. (See bubble size legend below.) This is why Monroe County is so important to the 29th. Obviously, it’s not everything, but it’s a big ol’ chunk. Probably not what the Republicans had in mind when they agreed to it.
100,000
50,000
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I did some work for Rocwiki using Google’s map API. The API lets you draw lines that have lat/long coordinates. But it would be a non-trivial task to do that with a congressional district because the gerrymander is all over the place. You can also place markers at lat/long points, and those markers can be any arbitrary png, so you could in theory place pie charts on a map. But from the looks of what you’ve done, the Microsoft software is much higher level.
BTW, I think your bottom map makes the point about the importance of Monroe to this election quite eloquently.
Trying to find a simple way to do anything in terms of districts and elections generally I have found to be an impossiblity. For example, I wanted to be able to have someone put their zip code in and find every representative they have, but NOTHING is broken down in this way. Congressional districts are broken down more or less by township, which is a start, but once you get into the city, things go street by street. Neither has anything to do with zip code, so I’m back to sqare one.