I know Scotland’s weather is a lottery and the midges are a summer thing, so I’m after the least-worst window for the Highlands and islands. May and September keep coming up - which gives the better mix of daylight, dry-ish days and open sights, and is one clearly worth it over the other? Real experience, not ‘pack a raincoat’.
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I’m Scottish, from the Highlands, and to be completely honest it is a bit of a lottery!
May has much longer days than September but also it’s the start of midge season.
September is a bit warmer but usually has more rain towards the end of the month.
Saying this though, the weather changes a lot between each day, or even each hour. In both months you could have weeks of constant rain, or weeks of constant sunshine so my advice is always to pack layers (and ensure one is a raincoat…) as even the forecast can change in a few hours.
If you go in with low expectations about the weather, I’m sure you will be blown away, hopefully not literally!
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May is probably the better choice if longer days and more time outdoors matter. September can be lovely too, especially early in the month. You get all four seasons in a day, mostly, 
but it’s often just moody showers that clear up pretty quickly. The Highlands and islands can change fast, so a good waterproof jacket is definitely worth packing.
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I can only speak from my time when I visited- it was early September, and it was honestly great weather! Sunny warm days and cooler evenings, but nothing a light jacket couldn’t fix (I am Canadian though, so bear my cold standards in mind!).