It would be useful if OP stated what equipment he had other than saying has 2 tractors already for the work he intends to do.
Perhaps a better explanation is in order.
I have an 8' York rake with scarifier, gauge wheels and blade that I use behind one of the tractors for grade work. The combination works fine for maintaining the road surface.
The ditches are the main problem. Due to steep slopes, soft ground and all the rain & snow we get, they are a real chore to keep clean. I have to do the work 3 or 4 times a year and sometimes more if we get a lot of rain. The road is 12' wide with banks trees and guardrails in some locations on each side. Due to the tractors length, it's difficult to maneuver when using the FEL while working perpendicular to the roadway.
I tried renting a grader with an angling blade that pulls material out of the ditch and onto the road surface. The problem is, it's mostly soft mud which fouls the roadway. The spoils need to be carried away or scooped and dumped back on the slope above the ditch. If there is a tow behind implement that will do this, I'm all ears.
For years, I used a small tractor, which worked ok on the ditches using the scoop & dump method. Due to it's size and limited FEL capacity, the job took forever. I have a wide bucket for the backhoe on one tractor but it is also tough to maneuver and the ditch work goes slowly.
There is a development across the valley with a road similar to mine. Once or twice a year, the property owners hire a contractor who cleans the ditches with a skid steer or grade all. Due to it's shorter length and small turning circle, he does in a day what it takes me three to do. Yes, the SS makes a mess of the road surface, but a couple of passes with a rake cleans it up nicely.
The contractor, the only one in the area that does this kind of work, charges $2500/day, including equipment transport. There are 12 people in the development who share the expense. Sure, I could hire him to do the work but I would have to pay the whole cost myself.
Doing the math, I decided buying another machine would be cheaper in the long run. This is especially true if you consider the trade in value of the machine.
I have no experience with a skid steer but watching that contractor use his, makes it look like the ideal machine for the job.