It won't be completely random, but you can use nested dynamic groups to accomplish your goal.
Example with 2 locations (add a new DG in the Master for every additional possible starting location, and adjust POI % accordingly)
DG Master (2 objects, minimum 2 maximum 2, 100%)
---DG CVBG loc 1 (X objects, minimum X, maximum X, POI 50%)
-----CVN loc 1
-----DDG 1 loc 1
-----DDG 2 loc 1
-----etc.
---DG CVBG loc 2 (X objects, minimum X, maximum X, POI 50%)
-----CVN loc 2
-----DDG 1 loc 2
-----DDG 2 loc 2
-----etc.
It can be a real time consuming PITA, especially if you have triggers and scripts for each of those ships, but it works.
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