I've been thinking about this since I heard of DC's 5G plan and I honestly hate Damian Wayne but the only way I can see him working without feeling like a complete usurper still to the mantle of Robin is if Damian was the second and final Robin. Meaning retcon Jason and Tim completely out of existence and make Dick the only Robin before Damian. Because of the nature of his lineage and the how he interacts with the rest of the batfamily (also where he's placed within the Robin lineage), Damian is best suited for the role of second Robin. The best (and only tolerable) example is in DC's current animated universe based on the New 52, where this plays out exactly. The problem with Damian is that being the fourth Robin is ludicrous while three Robins aren't a stretch if Jason Todd is only around for a year. But the thing is, Damian's personality and relationship to Bruce would only serve to reinforce the idea that Batman should NOT have another Robin after Jason's death. Whereas Tim Drake was expressly created with the intention to drive home the fact that Batman needs Robin. So with that in mind, it would only make sense to either retcon out Jason and Tim entirely to satisfy the conditions of having Damian at all and to ensure logical consistency regarding the passage of time and how aging works or to remove Damian and have Tim Drake reinstated as the third and final Robin.

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But if DC were to do another reboot, which is likely sooner rather than later, they should go full bore and start from zero. Complete zero. None of this half assed New 52 "some stories are canon but some parts of those stories aren't but then other stories are canon" nonsense. You can start with everyone in their first or second year as heroes and go from there. Ultimately this means that Batman is alone, with only Alfred, Lucius Fox, and Gordon, maybe he's still antagonistic with the police. But then introduce Dick Grayson as Robin for the first time and stick with that for about four to five publishing years. Have him graduate to Nightwing and then you can go one of two ways: 1) Jason Todd Robin followed by Tim Drake then stop or 2) Damian Wayne Robin then stop. Either way you could make DC's "Ultimate" versions of these characters which would help to curb the massive continuity issues and spark more interest in the medium again as the New 52 did commercially in 2011 and what the Ultimate Universe did for Marvel in 2000, before Loeb touched it with Ultimates 3 and Ultimatum.