Hey lexm,
welcome to the Strida Forum and many thanks for the interesting impressions of Chicago.
I am sorry you are having trouble with the handlebar release button, I disliked this part too and changed it.
The picture series to be found here: mobile01.com/topicdetail.php?f=317&t=1630057 contains a lot of informative pics (starting with picture 16) to change the button to another style, maybe this will help to solve your problem? The person shown took the “long way”, coming from the end of the grip, removing the bar-end plug only.
In case of bended handlebars this way will be impossible, you will have to remove the handlebars as shown in steps 5 and 6 below:
Best regards