Mapping Software Recommednation

[Frankl]

Even in illustrator I have to manually adjust whatever data I pull in to strip the unnecessary info, and reshape it to be a "non-proportional" map. I'm just curious if anything exists like (now long gone) MSN Maps 'Back of Napkin' stuff (there's a link above if you want to see exactly what I'm talking about) that you just plug in the two addresses and it does the rest for you.

Even if that doesn't exist, If you have any recommendations on how to work more efficiently in Illustrator that would be fantastic.

[Hai-Etlik]

Go to OpenStreetMap, find the area you want, select "Share" from the toolbar on the right, pick SVG or PDF, change scale and bounding box if you want, "Download". Open the file in your vector graphics editor. This should be a lot easier than tracing a screenshot. The exported map is licensed under Creative Commons-Attribution-Share Alike, the raw information being presented is under the ODC ODBL (if you trace it or strip out all the styling and symbols, you should only need to follow the ODBL, not the CC license.)

Using a GIS is much more fire and forget once you have it set up. If you use say the OpenStreetMap plugin for QGIS and set up your own symbology and print composer, then for any new map you can just grab the data for the area, apply the symbology you already created, run it though the existing composer, and have a finished map in, anywhere from a few minutes to a few seconds. As GIS workflows go, that's very basic, but it still takes a bit of learning to get to there from only knowing graphics software.