I have two of the ankle braces that you linked to in your post but I have the speed lacer version. Very easy to put on and take off. Love them. I wear gel sleeves underneath. They are long so I put it on with part of it almost under my heel and double up the extra so there’s a lot of cushion around my ankle. Tip- put on inside out and flip over. That way the gel doesn’t stick to your skin while you’re pulling it on.
Silipos 10845 Gel Tubing Ankle Sleeve, 3 Inch x 1... https://www.amazon.com/dp/B00JFTW43I/ref=cm_sw_r_sms_api_glt_fabc_GSRY39XSTNYJ8FNA5PRW?_encoding=UTF8&psc=1
Common problem. Buy this thing, cut in half, wear with the gel side facing in.
For the problem on your actual foot, you probably need to punch the boot out there.