Re: rigging question
Typically your upper shouds should be tight enough so that under load the leeward shroud goes a bit slack but not floppy when the rig is loaded up.( A rigger friend of mine said they should go just loose enough that you could pull the pin out.) The lowers are less critical but using the same rule will ensure that the mast stays in column under load.
1979 Santana 30 Tall Rig