There are a few fundamental rules about drainage that should help. With regard to roads, I think it was Eddie Walker who wrote here years ago that if you don't have two ditches, you have one --- right down the middle of your road. You absolutely have to build your road bed up to the point that a heavy downpour runs off the crown and down the ditch. I happen to be lucky enough that my road is a constant slope, with no point at which it dips. I do have a dry wash that runs across the road, which really gets rolling in a good rain. When we first moved here the culvert that the previous owners had installed for the dry wash was completely inadequate. After two springs of watching our gravel disappear and the road become impassable, I ripped the culvert out and replaced it with one three times the size and capable of moving the same volume of water the dry wash could carry.
I've also cut in several French drains, etc. for the yard. One of the best things I did for a soggy patch in the yard was to give up and make it a wet garden. With both surface swales and underground drainage I have all the water moving to one point, where I have planted a mass of native flowers and bushes that all like "wet feet". The plants move the water out of the ground through transpiration faster than grass ever could. If you have several boggy spots in the yard, channel all of them to one spot with drainage pipe and put a wet garden in the collection point. I put an overflow drain in the wet garden that runs to the dry wash for the real toad stranglers.