Based on my specific problem, would it still be still be easier to use Unity's terrain system or sculp it in 3ds Max

A bit of background to my project
I am trying to develop a game, which takes place in a make believe suburb. The major sceneries are, a housing development, 3 schools, (elementary, middle, and high school), graveyard, and a tree house. I have recently finished blocking out the high school building and its props in 3ds Max. With the high school, it is designed to sit on a prop of hilly land. In addition, I have made some foundation supports within my blockout design to help support the dirt and grass in high altitude areas where I am flattening the surface.

The problem
However, even with flattening the surface, there are still some areas that require my pavements and roads to go up hills, and I find it kind of hard to get the terrain to fit underneath so that I can place my pavements and roads on top of the terrain.

I have no experience in doing this kind of work, and everything I find on the internet are things about simple stuff, like what each tool in the terrain editor does and how to create a terrain, which I already know. However, there is nothing about strategy. So I am wondering which would be better? I would like to use Unity’s terrain editor, so that I could use its tree asset package, but it seems like 3ds Max’s sculpting tools do not have this issue.

I have once heard of building smaller terrains around your objects, but is it possible to make a terrain small enough that would fit inside a foundation bed, say like a garden in front of a school building?

So, the problem is you find it difficult to raise/lower Unity terrain to match up with your modelled terrain? Just practice more with the terrain tools. There’s a slider to lower the sensitivity, which helps a lot (you can brush, brush, brush to gradually change it.)

Owen, I think the terrain tool is too hard for me. I even saw someone reply in a different thread. The replier actually said that the terrain tool is really only made for distance or blockouts, and you would be better off using a 3d modeling program. I guess I should of mentioned that my high school landscape is for close-up, which the player will be walking on the pavement, and the smallest gap or overlap of the terrain is just going to show up as the designer did not care or is inexperienced. So for now, just like the other replier has mentioned, I think it would suite me best as well to use 3ds Max instead.