They mean each entry on a new visa. So if you enter as a tourist, you can get the 60-day visiting Thai family extension. Then you leave Thailand, and enter again with a non-O, you can get the 60-day visiting Thai family extension. Leave again and enter with another visa, etc... But if you're on a string of extensions based on the same entry, you're not getting another 60-day visiting Thai family extension. These extensions PLUS the old Multiple entry non-O marriage visa used to be how people lived in Thailand 5-10 years ago. Hop over to Laos (who didn't require proof of funds for the visa application) and get Multiple Entry non-O same day. Come back to Thailand and get 90 days on entry, then apply for the 60-day family extension. After 5 months, do a border bounce and repeat (since it's a completely new entry since it's a multiple entry visa, the old permission to stay expired already). That's 10 months, giving you enough time to do it one more time, for 15 months total. Then back to Laos for another non-O. If you lived close to a border, pretty simple way of avoiding any financial requirements.
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