You can obtain more clearance near your CMM's axis boundries by modifying the 'Check' distance. The lower the values the closer to the axis limitations you can utilize. It seems however based on the information that you may need to move your product more central to the workspace as you are only at point 3 before it is erroring out.
That or you may have a calibration issue on the tip you are trying to use?
Another trick is to use different angles so that you can reach further. You can rotate your A-axis for the section of the cylinder you are having trouble probing to get that extra little bit of reach. For a big cylinder that lies beyond the CMM's reach, you could use A-45B0 for Y+ quadrant, A-45B90 for X- quadrant, A-45B180 for Y- quadrant, and A-45B-90 for X+ quadrant, then construct a cylinder from all the hits of each cylinder
Maybe I'm mentally picturing this scenario all FUBAR, but if you can manually probe it... hmmm.
Do you have an 'avoidance move' ON? Personally, am not a big fan of that option in auto-features::::::