Upvote:6
What should I do?
If you are traveling so soon that you need to submit the ESTA application before you receive an answer from support, list the most recent passport or national ID card from each non-VWP country, then list the two next-most-recently-issued expired or stolen documents from those countries, and submit your application.
Would I have any problems if I omit the oldest one (stolen and expired), and mention the other four?
It's extremely unlikely.
Or do I need to give up thinking about ESTA and get a visa instead?
Only if your ESTA application is denied.