I won't face this for a few years, but I'm curious whether it's done at immigration in Thailand, online through the e-visa portal, or through the issuing consulate in the home country...
DTV is great, but it's still necessary to leave the country periodically.
Since you already have a house there, may I ask what visa you have used until now?
If you do get the DTV and choose to extend the visa in order to stay up to 360 days, then be aware that you will almost certainly need to prove you are still attending the Thai school and have the required funds.
Tofu Chili Even if it's a parting gesture, a letter from the current employer stating the 'current' employment status and the ability to work remotely will do it.
If you can get this, do NOT mention you're leaving in November, because that will complicate matters.
It should be on their letterhead and/or stamped, signed by someone senior enough to do so.
It will be significantly more difficult for you to apply, once the employment has ended.
In the meantime, get your new business structure fully up and running. There's no reason to delay that! :-)
that may be needed to support the intended travel date, which you indicate as part of the application. If your travel date is fairly soon, they may need to prioritise it and may want justification for that.