To trim or not to trim?

I try to schedule my hair appointments for color every 6 weeks (it's a must with red). I have to admit though sometimes most of the time life happens and 6 weeks turns into 12. I'm finally going in for a much needed root touch up. I'm trying to work up the courage to get a trim to get rid of my damaged ends. But after 5 years of not letting scissors come in contact with my hair I've developed a small phobia of getting a hair cut. Below are images of the length I'm considering. Towards the end of last summer my hair became pretty unbearable so I think this length is the perfect compromise during the hot summer months.

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