I used Inkscape to draw a map of our village. (*)
http://xmodem.net/lif/pleasantville.svg
This was after the fact, and was extremely difficult with just "Observe" - though became easier when I learned to do "Observe" / / "C"
which puts you down to eye level instead of jerkily jumping around from building to tree etc where too much land is obscured.
(*) Only 2D. A Work In progress; Green circles for trees, with "A"pple and "M"ulbery indicated (and 2 "Ma"ple). I have to add 3 farm fields, etc - it is a never-ending chore!!
P.S. with, for example Inkscape, if we had a set of templates, i.e. the N x M of each building that we could duplicate and drag into place, this would become a modest planning tool.