"Fighting the compiler" doesn't necessarily mean type errors. It could mean that you have to warp your design to fit the constraints of a language, often making much more extensive changes to your program than you would otherwise would've had to.

Though a lot of my complaints about Haskell's type system could be alleviated with a good integrated refactoring tool. If I had one-command operations to:

a.) Convert a plain function to a monadic one

b.) Change the signature and stacking order of a large stack of monadic transformers

c.) Add a new alternative to an algebraic data type, and track down and fix all functions that use it.

d.) Add a new parameter, at an arbitrary position, to a function.

e.) Change a straight return value to a Maybe.

f.) Add a new field to a record or tuple type.

Then I'd find Haskell's type system much less oppressive. What's the status of Leksah these days?