It would absolutely make sense, in your stated case, from a user perspective to buy elite visa now over just using DTV/tourist now. Especially if bringing in animals. DTV is by no means whatsoever a residency visa. Yes, Elite is not cheap, but if you consider the cost per year with no hassles and the stability you want in Thailand, it seems to be the clear answer.
a O-visa retirement extension costs 1900 per year. 365 days. Every single border bounce from a place like Samui cost 4500 baht. for 60 days. Plus 1900 baht for a 30 days extension. Break out your calculator and let us know which one is most cost effective?