It may be that previous owners have used the mainsail without the jib (I do it as my "first reef" as wind increases) enough that the main is more stretched out than the jib, so the jib is able to "outpoint" the main. The jib on the DS is sometimes difficult to trim due to it's size compared to the main and the way the jibsheets are rigged. I have found that what seems like a tiny adjustment of the jib sheet results in a big difference in trim. The mid-boom mainsheet is not perfect, really could use a traveler, but works and is less trouble than end-boom sheeting. Unless you are going to rig the end-boom sheeting to a rope traveler (fixed position or adjustable), at best I think you will find little improvement over the mid-boom without adding more complication. Worth doing if you race, but I doubt the added complication will result in that much benefit for "daysailing".
I think as others have said, that the real problem is older sails that may be stretched out. I do agree that adding a boom-vang if you don't already have one is a big help! It will hold the boom down, flattening the sail plus that results in more of the pull of the mainsheet going to pull the boom towards the centerline, less serving to pull the boom downward. I find it much harder to trim the main in the last few inches if my boom-vang is loose.
So, try easing the jib sheet ever so slightly to open up the slot between main and jib, lay off a couple of degrees ,and you should find things work better. I'll include a page from my DS II Owners Manual showing ideas for how O'Day originally had the mainsheet set up prior to switching to the mid-boom, and how some owners have modified their end-boom setups.