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Genuine answer: it depends. I guess you just have to be present and observe what is going on and try to get closer to what you try to achieve.

What works all the time is to not cut the whole place at once: so insects have another places to move to. I am also trying to make sure grasses don't take over the place.

But the thing is: even on my few acres spread in diameter of few kilometers I am getting very different results.

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Few kilometres, amount of shade, amount of water in the soil, different type of soil, different history (e.g. used to be farmland or used to be forest) can all be reasons for different results. But yes definitely don't cut everything at once, that ruins the habitat. For the rest main problem is usually nitrogen deposition so key is cutting and removing cuttings to compensate for that i.e. remove nitrogen again. And the time at which mowing gets done is pretty crucial as well and requires some experience with the specific terrain as you point out. But there's way to much nuances to all explain here. By far the easiest way to gain knwoledge imo is finding a local nature organization which manages grasslands in your neighbourhood and see what they do/talk to them. I did that a couple of years and it's amazing what I learned from them (though in all honesty the people there are true specialists when it comes grassland and it's fauna specialists, it's also their daytime job, and there's like nothing they do not know - not everybody is that lucky)

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