275'? Holy crap I wouldn't want to be the one reeling in that rig, lol! Dave which size Dipsy do you have? On a #3 setting this spring I was hitting bottom in 50ft of water running maybe 125ft-150ft out (40lb PP on my setups).
I also like letting the dipsys out on the clicker instead of free spool, they'll tangle if they just drop right to the bottom (Or so I've found)