advice from an adjuster that has seen this before

hit a pot hole in a construction zone that was unmarked and un protected. It was a county project. I have evidence to prove they knew about the pot hole and the construction company caused the hole to re-open with their equipment. However, they are both denying my claim. The construction company had sub-contractors milling the road. Do I sue the county and the main construction company or do I sue everyone that I know stepped foot on the grounds (i.e. water companies, sub contractors, etc.)? Or, should the main construction company and the county be good enough?

How likely is it that the County and/or the construction company will settle out of court?

(The claim is worth approx. $1000.00)

Can I add in the suit for loss of my time researching this case over the last several months?