Consider the example of digitizing along a line of latitude in an east-west direction using geographic coordinates (aka, a GCS with a WGS-84 datum). If you just pick a start and end point, then project the data, there is a chance that the intervening space will not follow that line of latitude. To ensure that it approximates the line of latitude, when projected, you need to densify your point creation,
In short the distance between lines of longitude along lines of latitude decrease as you head poleward. This is a fact about trying to approximate a sphere/ellipsoid/geoid in planar coordinates.
In your case, you might have been better off digitizing your map using the projected coordinate system rather than the unprojected (geographic) coordinate system
... sort of retired...