I can understand your concern on this as some of the Thai consulate websites state only two entries per year on visa exempt but this doesn't appear to be the case in real life. Don't stress it unless you've had problems with immigration or have entered Thailand repeatedly
If you're income could be considered remote then why would you use the soft qualifications. The DTV has nothing to do with retirement age. Just prove you've got the ability to earn income remotely, have a minimal bank balance and a few other details and done... 5 year multi entry visa.