I have a water softener connected right after the well tank so everything goes through it (unless I close the bypass valve then everything would be unsoftened.) I have hard water with (I believe soluble) iron in it.

I got the initial fill trucked in as a 24' round (13500 gal) demand sounded like way too much for a well pump.

I just got the pool installed so I don't have much experience to pass on but from what I have researched, I believe it is better to remove things like iron and other minerals BEFORE they go into the pool rather than after the fact.

You might want to consider adding a separate feed after your water softener just for pool use.