Well for example, I'm a lead devops on a team of 2-3. We have 6 core services.

For the last several years, due to static load we've been fine with 2 instances per service. Now that we want autoscale (even though all the real load is really just the DB), it seems we could get ourselves onto AWS autoscale in ~1 month, though it would require some coding.

Spending 3 devops on 1 year doing something is a red-flag to me. If your changes save devs 1 hour per deploy, it'll pay off 6,000 deploys from now.