I voted for May because I'm thinking - which might be incorrect - that the midges in Scotland won't be about that early and riders, volunteers, helpers and organisers might not get bitten as much while waiting around.
May not be a good idea to go over a bank holiday weekend way too much traffic., also may be worth checking on the history of wind direction for the periods you are thinking about.
Whilst not wanting to be involved in your attempt, I hope you do not mind mt small inputs.
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