Welcome choppinIt.

Which format are these maps in? If they are just flat images, such as scans of the original WWII-era maps, I don't think there will be any good options other than hand tracing then.

While Sue's method is a good general method for doing this, restoring the outline of entities drawn with a drawing tool is even easier. Just right click :CC2MCHANGE: and pick change like draw tool, Now, the command line prompts for a drawing tool. Right click inside the drawing window to bring up the list of tool, and pick the landmass tool. Then select the entity, and Do it. This restores the appearance to that of the tool.

Sounds like you are not running with the latest update. The hammer icon should supply four options (small, medium, large, x-large), the single option for just large icons was replaced a while ago now, along with fixes to make things work better on high resolution displays.

Remember, you should always (re-)install the update after installing add-ons.

Easiest is to just install patch 3. Unless I remember incorrectly, Patch 3 doesn't require the CD, and should be the only one you need (see my previous answer above)

It looks to me that the wall has been turned into a smooth poly? Trace do have problem following smooth polys because the actual shape of a smooth poly is calculated from the nodes, and not actually going through the nodes. It does some attempt at a simple approximation of the main shape, but that rarely works out for complex entities.