Wet area recommendations

[RBLapham]

What is on the back or other side of the barn? might be easier to run drain there instead of under driveway. Pipe is cheap, driveway no so much.
Plant cattails

 

[CobyRupert]

At $65/hr, I'd be looking around the property to see if there's 10 other jobs he could do as long as he's already there.

 

[leveled]

You need a rotary level and figure out where you can let that water out, Unless it obvious with your eye. Looking at your picture, I would dig a trench around the build and go through the driveway, and let it out somewhere or into another drainage ditch. You could also tie your gutters into that also. I would take grade sticks a put them every 10 ft and figure out the available pitch and lay it out before he comes in with the excavator. have him dig it while you work the level and it probably wont be more than a two hour dig.

 

[Sonny580]

Wish it were $65. per hour here! lol! --- anywhere from $95. to $175. depending on who you get.

 

[MechanicalGuy]

a gutter for the roof would be very cheap and centralize all the runoff into one spot.