It sounds as if you would like to sign a long-term contract with one provider. I suggest you give this contractor time to show the quality of service.

Our road association had a similar problem. We have settled on a preferred contractor for road maintenance and repair including culvert replacement as necessary. There is nothing in writing but this "long term" relationship seems to benefit both parties --phone calls are returned and jobs handled pretty much as they arise (with consideration given to busy schedules, etc.)

We do make sure we pay promptly. In the spring, we request road maintenance. Our contractor inspects the road and sends us an estimate for cost of repairs listing the work proposed.

We have separate contractors for winter plowing and culvert cleaning and trimming at entrances in the summer.  In our area, it is not uncommon to find someone who plows in winter and does yard work in summer.