Agree with HM. If you have the weaners wormed before you collect them and only keep them for 5 months,then the land/pigs should be ok. I think (someone put me right) that you don't worm for one month before slaughter and that the worming injection lasts 4 months. The butcher/abbatoir will check the liver for worms and let you know.
With a 40 x 9 area,you could partition it into two 20x9's leaving one area free from pigs from mid-August onwards,giving you enough time to rake it down and reseed. I nearly got caught out by the weather last year,but managed to get it reseeded and just about established to over-winter.....Ree