I'll go along with Stir;ling - having looked at the road runner file you posted, there is only two z positions, one is Z0.2 and the other is Z-0.1. This is the first time I have looked at this file, and I am suprised to see that there is an entry for X,Y and Z on each line.
It doesn't actually matter, though, because the tool should only move if it is different to the previous entry for that axis.
As Stirling says - and you can check this - the first movement is 0.2 and should be up, the only other movement is -0.1 which is 0.3 down from its upper position.
When you have jogged your axis, I assume you put the x and y at the start position, touching the work, and the Z axis is positioned with the tool just touching the surface of the work. DO NOT FORGET to ZERO the Z at this position.
The first move should be up - away from the work, and the second movement should be down. If it is the opposite way check your ports and pins and check the direction pin for the Z axis. If it is checked for active 0, uncheck it, and vica versa, and the direction will alter.
I read you first post again, and I think where you are going wrong is messing about with the Z axis at all. Clear all your offsets, particularly tool depths etc. To get going, merely touch the tool tip on top of the work and set Z DRO at 0. This will tell the machine where it is (in relation to the depth). As we said - from there it should go 0.2 up, move, then go down to position -0.1 which is 0.1 into the work (since you set the top of the work at 0).