Chasemixon - your description makes perfect sense. It might be that my topping lift (the line that holds up the end of the boom) is shorter than yours. I have a small block that is attached to the topping lift to raise and lower the end of the boom. The tail is made fast to the end of the boom, through the block, then over a sheeve in the boom, then forward to toward the mast, were it exits the boom, and through a couple blocks comes back to the cabin top at the winch area. ( i attached a drawing of it) if you need a pic, it can stop by the boat this week.
Not pictured is the outhaul, which connects to the sail, to make the foot tighter/looser. I have a drawing for how its run through the boom if you need that.
When under sail, your topping lift should be loose, and not holding up the boom, that is the job of the sail. You don't want it flogging the sail, just not holding up the boom. And yes then the mainsheet and boom vang are pulling down on the mast.