--> "How do you get around this?"
I'm not sure why you say "Take from context" is so powerful.
I've used this a lot - but I create a JSON_String field/object in the User Table or the new NP in-memory table... building a string to match the endpoint requirements and then I use "Take from context" specifying that table and field that has the JSON.
So if I didn't need the quotes then I'd leave them out on the boolean element and it would work fine.
I also think if he "fixed" this for boolean, the next person might come across an API that needs quotes around ALL elements and now they couldn't use it.
I also think I'd never use "Take from context" using the "None" attribute (as you must be doing) because then all fields from that table would be sent to that API and what about extra fields you don't want to send them? Yes, you can exclude some fields in the service, but that might be a huge list to exclude in some cases - I just don't think I'd ever use "None" as I'm happy building my JSON string into a tmp field.
So thats why I don't think "Take from context" using NONE is that powerful, unless you have a better reason.