There's too many specifics here: we have no access to your Sitecore implementation, your HTML or your business requirements.
Yes, sites have successfully been migrated in and out of Sitcore/various CMSs, some will use the API to retrieve data, others may use crawler and HTMLAgilityPack to parse HTML, depends on your current content structure. How do you deal with shared content for example? What about migrating internal links, or links to media? Are you doing a like-for-like migration or is the site also getting a redesign? How competent are Content Editors? Maybe you can do a first pass migration with automation but more than likely somewhere down the line some manual intervention will be needed or you will need some more automation to fix something which you initially overlooked.
So it's going to depend on exactly how much content you have, and how much time/effort it is to automate vs manual re-entry.
As LittleBobbyTables says, it will just be opinion as none of us have the facts you have at your disposal.
To answer your question directly, yes I have worked on automated migration, but for very specific areas of the site and everything I say above had to be taken into account, we went back over the content several times because sample content looked fine but some content had weird formatting etc. Difficult to do in a very generic way.