I have the Jimmy Choo Love heels in suede nude and they are very comfortable.
I remember trying on both the Love and the Romy heels when I was in the store and I recall that the Love covers the toes more while the Romy shoes more toe cleavage.
The greater surface area of the Love may provide more support but after a while, they may feel relatively uncomfortable (as your feet swell) if you're not used to wearing heels for long periods of time.
I highly recommend trying them on in stores and walking/standing in them for a while, if you have not done so yet.
Generally the easiest to break in are suede, then calfskin, and the hardest is patent leather. (Fabric/mesh/plastic depends)
I don't want to say too much because I wear heels on a semi-regular basis. I am very used to wearing heels for long periods of time, and I prefer to wear heels that are 3 - 5 inches in length. I also can tolerate some uncomfortable heels and so my threshold for pain and discomfort may be higher than yours.
Taking in your medical history, I don't want to give you too much hope and just say it's fine to jump into it. If you haven't done so yet, maybe ease into it with more form fitting shoes/flats, then a low heel, etc. If you can wear those without much issue, then it's easier to take the plunge into designer heels.
Hope that helps! Good luck!