The best way to create roads and railways is use the editors default button "Create All" after you have placed all the fields, factories, cities etc. to your terrain.
It makes automatically 10 miles long tracks and roads with the convoys and trains to your terrain. All the paths are going straight to south from your targets, but then you can manually place them where you wish.
After every road changes you must push the "Redo Objects" and the editor is situating the convoys and trains to the new locations near the road's/track's first point.
If you do roads/tracks/rivers manually, you must use the editor's default convoy/train/barge Shape Groups and put them near the first points of the paths. Also after this method you must ALWAYS use "Redo Objects".
From the "Road Properties" you must check that fields (which use only the Roads) has correct destination numbers (field's number). Factories and HQ's must use the "Radius" which default setting is 0.5 miles.
Check also that the roads' and tracks' last points are in the same mile square where the destination field or factory is!
You must use the "Redo Objects" button also every time after you have made any elevation adjustments under the roads'/tracks' ways!
Notice:
Convoys, trains and barges are going their ways in 10 minutes regardless the tracks length. So don't make too long roads or you have really fast trains and trucks!
Suitable values are 7-10 miles to roads and railways and 3-4 miles to rivers.
There's an example picture from Radar Factory and "Road Properties" values:
Ps. If you want more roads as "eye candies" to your terrain, then you can use the "Visual Only" check mark. You can for ex. make "visual Only" road extensions to your supply roads or railways.