@Jacob Veasey Thanks for reaching out. As per your analysis, you have mentioned that when there is less function than it works fine where with the larger number of functions in a single function app you get 500 errors.
It looks like there might be resource crunch issue such as memory where you might be getting out of memory exception resulting in 500 errors as the consumption plan has limited memory similarly if you are using app service plan then also it will have a limit of memory.
This could be one of the possible causes as per the analysis that you have observed. To know the cause of the issue/more details on the 500 error I will suggest you to review the Diagnose and solve problem blade on your function app to troubleshoot the 500 error and the action plan to resolve the issue if there are any. You can also review the application insights logs to know more details/exception trace on the 500 errors.
In case if you need any help in verifying the logs then please let me know.
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