How to choose correct running shoe drop?

I’m having a difficult time understanding why having a bigger heel on a shoe makes it harder to land mid or forefoot.

Perhaps I don’t understand what you are saying.
I’d agree with his assertion.
Forget the shoe for a moment and imagine the position of the foot when it makes contact with the ground.
I believe I land fairly flat. i.e my toes are level with or slightly below my heel. I prefer for my foot to take the initial load evenly or slightly forward. Probably what would be called a mid-foot strike. Now superimpose soles with various degrees of heel toe drop onto that foot position:

Flat sole → The base of the sole will be parallel with the underside of my foot. Thus my level or slightly toe down foot translates into a similar shoe undersurface orientation which means I will load my foot accordingly.Slight heel to toe drop → The sole will no longer be parallel with my foot but rather lower at the back. Thus the any slight toe down approach to the ground is now reduced, neutralised or reversed. The heel is now closer to the ground and a mid foot strike will tend to be influenced towards a heelstrike unless the angle of the foot is adjusted to compensate.Large heel to toe drop → As above but more pronounced. In my case, it’s very difficult to run the way I like with a large heel toe drop. I tend to make contact with my heels too early and find it difficult if not impossible to comfortably compensate by adjusting my gait.
I’m not a great runner but my gait works reasonably well for me in bare feet or zero/low drop shoes. High drop shoes make me very uncomfortable. I originally ran in them and my gait was terrible. Eventually after injury problems I switched to zero drop and made some major changes to my very poor running posture. I’m far more comfortable and have virtually no injury issues now. I have on occasion tried running in more conventional high drop shoes again and can’t maintain the style I now find so much more natural and comfortable.

Incidentally, I understand that how the foot is loaded is not quite as simple as angle of foot and is largely coupled with both vertical motion and position of contact point relative to centre of mass. However, when everything else is sorted, the shoe is capable of screwing it up again and a high drop will screw it up in the direction of heel striking if clearance is not already sufficient.