Plot hole: Modern diabetes management will tell a patient immediately if their glucose levels are out of the ordinary. Results are not monitored and delivered to a county jail by an outside lab. If a diabetic is sick enough, they would have obvious physical indications. The entire escape plan hinges upon these fallacies.
Plot hole: Milo and Nicole go to the club and ask for John. After failing to convince the woman that he works in the senate for Kansas, the woman looks at him and calls him 'Senator' but calls Nicole 'Mrs Boyd'. There was no mention any of their names (even though Milo's surname is Boyd). If the woman calls Nicole Mrs Boyd, she surely must know Milo and that Nicole was his wife.
Suggested correction: The scene starts with the membership director telling them the club is closed for a private event, so we don't see them enter and what they say to her. They obviously cut straight to this part to cut out time. But Milo and Nicole would have given her their names so she could check to see if they're members or on the list.