I would love if pyannotate could fall back to dympy suggest if no type info is found for a function. I'd be happy to submit a PR for this (I've already created a prototype that works as expected).
If you'd rather do something more abstract/configurable, this could be implemented as a shell command to run as a fallback:
pyannotate --signature-cmd='dmypy suggest --json {filename}:{lineno}' file1