Cannot delete hole

In the first case, the problem is that SONAR can't "delete hole" unless there's something in the range to delete that creates a hole. Crazy, I know, but it's always been that way. The simplest solution is just to select all the clips, and drag or copy-paste them back to the beginning of the project. If the earliest clip of the bunch doesn't start right on the grid, change your snap mode from Move To to Move By measures to preserve the offset.

I'm not sure about the second issue. You should have to have "shift by whole measures" selected. But I haven't used that function for a while, so I'd have to play around with it to see what might be happening. What time range are you selecting to delete, and what's in it for track content? 

I actually got it working by extending the beginning clip and cutting part of it out for the hole to delete. Seemed to work fine. I tried doing the select all and drag, but it threw my MIDI out of whack.. Thanks tho!

select MEASURE instead of musical time and see if that makes a difference