"John" wrote:

1. What kind of equipment should I get? Backhoe, trencher?

How about trenchless boring? They can do amazing things with those
devices these days, I see a whole lot less trenching than I used to.
Only a hole at each end.

Look for a contractor in your area.

Pulling a drain tile would seem to be a quite doable task, and a lot
less mess than digging.

I don't think you need to go down to that depth. Is the water surface
water (aka rain) or sub-terrain (like a spring)? At some point, your
going to being trying to drain the water table, which may not be a good
thing.

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