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Taking your second point first, looking at your process the design is breaking a design rule in that you cant have two preconditions in a row to move you automatically across 2 statuses ("Authorised" --> "Authorised3" path); there's a thread somewhere in the community about this limitation. It's a purposely added designer condition to stop potential endless loops at execution time. Only way around that is to redesign your process.
On the first point, you dont say what ITBM version you are on but if it's 7.3 or later you could create a calculated condition that checks each of the fields you want to monitor and returning true/false on which you can branch on in the process. I use these in my process to do complex branching of the sort you are trying to do too.
I'm currently on 7.2.6 but we should be upgrading soon. It looks like calculations will be the way to go then.
I would be interested to read the thread anyway though as its never made sense to me why you cannot use certain connections. Have you any idea what the title of the thread was?