Progress Report
3 trenches done, about 140' total. Perforated pipe laid down and covered with 3" rock. This should allow a lot more drainage, hopefully solving much of the ongoing problem. Of course since I'm laying in the pipe I did what umtallguy said and curved the end of the pipe up to the surface. Plan to place a 1' x 1' grate and drain box there but for the next few days the hose is just draining straight in.
Today my good neighbor came over with his
BX25 and scraped away all the clay brought up by the trencher. He spread out the rest of the 3" rock for the trailer parking area and flatened it out. Afterwards I drove over the whole surface to pack it down even more. Tomorrow the fabric goes down and then gravel.
I hear you guys, concrete is always an option and if this doesn't pan out then at least I'll know the foundation is best as possible when we do pour concrete. Being the most expensive option and one that tends to always crack I'll go that route if we must but doing that at the house just begs to do the whole area around 2 garage doors plus 90 yard long driveway so I've tried to not bust my wallet just yet. The trenches probably should have been done when the house was built but that was long before me.

Drain to daylight

Three trenches about 25' apart the last one is near the trees in the back.

You can see how the clay just piled onto the tires, it packed in all sorts of places we spent an hour cleaning out. Probably I should have rented a bobcat.

Smooth more so than level but having slope means drainage. I'll just have to border it so the gravel doesn't wash away.