I believe the amount of work you are asking for will exceed the payment offered? Your having to pay not only for the equipment rental, but the operator's time as well.
Difficult situation to be in. Managing land the proper way is expensive, and it doesn't keep itself up by itself.
Cover always grows into the road, or falls into the road.
Regardless, make sure if you do the road work or have someone else do it, the key thing for long time use is ditching the roads with good water turnouts. Flat blading roads while necessary in some situations, will wash the road at some point.
Once the roads are done, let the rain settle on them and stay off them when wet.
You may already know all of this.
Turn outs are what channels the water to run off the road, as seen to the left of the dozer blade.
Crown of road is what is seen here, the road built up in the middle, allowing water to go into the ditches and OFF the road surface. (The road runs to left down steep hill and turn out is seen to right).
Flat blading with slope to right is needed here, as there is NO place for the water to get off the road to the left, as the road is lower than the bank. So we have the water gradually move to the right to the turn outs.
As written, you may already know this, but if not, you need to know it. Continual grading of the roads and getting the road bed lower than the side of the banks is a No No, it only builds up a place for water to stand and form mud holes. Assuming you can't get your turn outs lower than the road beds.
God Bless,
David B.