Automating legacy products
From the lens of an automation architect
The front end is in some ways easy and hard to automate
Synchronization can be a problem but object identification can get easier
API automation can be a challenge, since they are not designed to be consumed for folks other than developers
Dev and test environment creation can be old school, that means creating and tearing them down is hard
More points under each of these areas can be explored here:
http://quality-spectrum.com/legacy-products-automation-technology-challenges/