Oh, i love all the inspo pics and am inspired and the inspiring Montreal blogger!
I agree with Stag Fash that heels are not necessarily uncomfortable -- but they are uncomfortable to some. My personal sweet spot is between 34/ inch and 2 inches -- lower or higher tend to be uncomfortable and to wear sneakers I need an insole to prevent against plantar fasciitis or I'm miserable, and truly flats sneakers like Cons are a nightmare for me -- the worst! A 4 inch heel would be better, no joke!
I do wear flatforms slightly better than complete flats (probably due to the padding). A lug sole works well on a flat.
i think those who've said you need to imagine the entire look to get away with a chunky shoe for evening are correct. Not always easy to do, but if you know it's what works for you, then you can plan for it going forward.