We have two sites on Umbraco 7 and Umbraco 8. The Umbraco 7 site is small, but the Umbraco 8 site is a more developed site, complete with product catalog, third party plug-ins, and forms. We need to bring these into modern Umbraco and would like to move to Umbraco Cloud if that makes sense.

What trade-offs are we facing by doing in-place upgrades from 7->8->9->10->Cloud vs recreating a new site in Cloud from scratch? Can we still import authored content into the new site or is that only a reasonable expectation if we follow the full migration path?