I have a 1988 Sammy with 2" shackle lift. As near as I can tell the shocks are stock. The leafs sit almost paralell to the ground at rest. It rides very rough almost no suspension travel at all it feels like. Would a better slightly longer shock help with this?

That depends, do you have any up travel left on the suspension?

 You also might want to be checking the shackles for binding, stuck/stiff shackles and crappy shackle angles. These things can cause a bad ride. How is the angle on the shackles?

If you look at the shackels from the side, they are pushed towards the front/back of the vehicle maybe 10 degrees or so. I am thinking there is not much suspension travel left with the way it is setup now. I think my best bet is to safe some cash and do the lift the proper way.

The lift was on the rig when i bought it. I would really like to drop the shackle lift and do it with some OME springs. I like the height of the ride the way it is. With the OME kit i would get the same height with decent ride I think.

If it is not pooring the rain tomorrow I will see if i can figure out if i am out of suspension travel.

Everyone I know who runs the OME springs likes them and mentions they are a better then stock ride.  It's a solid upgrade path if your are just looking for a little bit of lift.  And I agree with dropping the shackles, not a big fan of large shackle lifts as it throws your steering geometry off.