With regards to autonomous ships, problems with interpretation of Rule 5, lookout. The other perhaps greater problem might be with Rule 2, "the ordinary practice of seamen”.
This comparison of ships at sea to a board game seems very questionable.
There still remains the issue of seamanship however: how does an autonomous ship, or a vessel with an unmanned bridge, know what “precaution. may be required by the ordinary practice of seamen”? The answer,
I believe, will be provided by artificial intelligence (AI). Computers can be programmed to learn (think: Chess; Go) and it would appear therefore, that the technology may already exist to program a vessel computer to know what the practice of good seamanship requires.
What’s likely to happen is once it becomes apparent this problem can not be solved given the current parameters an attempt will be made to change the parameters of the problem.