Montages work because cinema can use visual data to establish the change in setting and timeframe and this lets the scene focus on action and dialog to communicate the story. This is not the case when writing since every scene change competes with action and dialog for setting.
I think that for you to pull this off you need to front load your montage with the settings and timeframes associated with your band dates or eyewear. This would let you use a shortened description to establish the new setting and timeframe with each new paragraph since you are only needing to remind the reader of information you’ve already provided.
Alice Munro uses a similar technique when she shifts time in her short stories.
To establish the intensity of a montage, the writing would need to use clear sharp and descriptive information.
I think transitions would present a challenge. Montages don’t need them, but writing very much does, especially in an essay. Similarly, Deep POV or stream of consciousness might give the intimacy needed to communicate to make this kind of story engaging. But, these two methods are very internal and don’t lend themselves to an external focused cinematic writing style.