Hi Keith,
The approach I feel should be you migrate or upgrade from 2016 to 2019 and slowly carry out a hybrid setup that will allow to migrate to Exchange Online. That will allow you to explore and mitigate any issues, detailed views on the features on Exch 2019 over here new-features
Also depends on your scope of work and how many users,mailboxes you have to migrate to Cloud needs lot of planning and assessment, it is doable but all depends how much time and efforts you can spend.
Features that are discontinued in Exch 2019 so consider all the options too. discontinued-features
Hope this helps.
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