Not a dumb question at all :) creating a world does seem overwhelming but I find it helps to have a Plan.
There are lots of ways of approaching this but, I suggest sketching out on paper a map of your world first, with areas the world will have, hills, valleys, swamp, rivers, lakes, beaches, etc, etc, add the colouring scheme, then draw in the roads and lots you want in those areas.
Next, in CAW, I would create the overall shape of the world based on your map, adding hills and other geographic features, paint the landscapes with your colours , then put in the roads and sculpt around the roads to make them fit into the landscape, then add the lots, adjusting the landscape around them if I needed to. ( I try to have lots of flat areas for lots.) After that I add trees, rocks, and other decorations.
How far apart to place lots is up to you and would probably depend on the area you are designing (dense downtown or sparse rural).
Anyway, others might do these in a different order, but this helps me to keep things organized. Of course, there will be a lot of tweaking so the order isn't hard and fast.
Hope this helps a little :)