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So I will answer my own question, with a "who knows what went wrong".
Starting with the init errors: my function had requests to things like parameter store in the cold start portion of the program, and those requests were timing out causing the function init to fail.
Those requests were timing out because of VPC config issues, and adding VPC endpoints for ssm fixed that. I also added endpoints for a bunch of services I make web requests to, and also added VPC gateways for S3 and Dynamo DB.
I was then still having intermittent web request failures to 3rd partys though, and it seemed like VPC issues was still the culprit, so I reorganized my VPC to look exactly like the template VPC that the new VPC wizard gives you
The important things here are the NAT gateway per AZ, and the NAT gateways are part of the public subnets. Then the routing table points the private subnets to these NAT gateways. The public subnets get routed to the Internet Gateway.
No idea why my config stopped working after 7 years, but it did, and those errors are definitely gone after correctly setting up my VPC and subnets.
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