So I tried to make a road and the game just always want to screw it up

The following screen is in fullbright.
I also did alpha blending with grass.

 Make a square.
Make it a patch 5 by 5  or any number.
Make it dirt
Click the patch in top view.
Press space to make a copy.
Line it up with your original dirt in top view. its usually 1 space over and 1 up
Make the second patch a blend.
With only the blend selected press v then y.
then select smooth  and alpha
holding alt while  you blend will un blend
Make sure you have a blend and a regular.
Right click on the  3d view to be sure you only have the blend selected..n
post if it doesn't work.

To adjust height select both patches and press v then y then click paint height and height. Must have both brushes selected or they will lift apart.

i did EXACTLY the same thing five times.

Use tile texture and grass blend. I did it as I typed this. some textures don't blend properly like ztoll rust.  Also make sure you press v then y. I got my first blend from the farmhouse prefab. 
 
Is a grid showing up when you make the patch?
Does the circle show up when you press y?
try to just adjust paint height.
Click paint height and height (the button under paint height.)
Make sure you se making a   patch....... simple terrain patch

Edited again .    don't make the patch much larger than a car parking space to start. You might be making it too large and  your inner and outer radius of the circle (from pressing y) is too small or large .  It took me a while to figure it out but once you get it you'll understand your mistake.
Post if it doesn't work.