If my plot holds water, would renting a ditch witch and digging a trench on both sides help it, or would I have to add soil to raise my plot?

How big is the plot and what shap is it in? If very big, depending on your soil type, I'm not sure if the trenching would help. Sounds like it is in a flat or bottom where the water won't drain away from the plot even with the trenching. To haul enough dirt to raise the plot level even a foot would take a LOT of dirt, depending on the size of the plot. I would instead hire a dozer and excavator and move the plot location higher on a natural rise. It will probably be worth the money in the long run.

Some drainage tile through the field could be a big help. More expensive than just a ditch, but much more effective.

Good idea with the drain tile or French drain. On one end of the plot you could dig a small pond area for the water to drain to, just make the drain trenches deeper than you till the soil. Depending on how well the soil will perk to the drains would determine how many drain trenches you would need to put in the plot.

They have a pond 100yds from my plot. Should I dig a trench on both sides of the plot leading to the pond?

Who is "they"? You can't just divert run off water into someone elses pond without them saying it's okay. I know I wouldn't want it in my pond.

Something you might need to consider is potential wetlands drainage violations. Not knowing what you have there makes it hard to give reliable, legal suggestions. Some states are much more vigilant in protection of wetlands. It can become VERY expensive if you are caught with a violation.

"I" have a pond Mr. F.B.I., that is 100yds from my plot. So would that work or do I have to take a lie detector test?

You're on your own kid. Someday you'll learn manners will get you a long way, and lying doesn' help anything either. I'm guessing "you" don't own squat.

Manners? I asked a simple question and you gave me a answer as if your the Army Core of Engineers. Why in the world would I dig a trench into a neighbors pond. "They" means I and 3 owners, own 8000 acres. I have my own bowhunting only sanctuary and there is a pond that was dug to build the levee system that runs thru our property, that I can run the trench to. If you don't have a intellegent answer, don't answer.