I'd be willing to bet no one has gotten an extension of the DTV at Koh Samui. Immigration offices DO NOT want to give extensions for DTV. And Koh Samui is known as one of the "rogue" immigration offices that does what it wants, regulations be damned. Reports from pretty much every immigration office are that the officers are telling people to do a border bounce (leave and return) to get a new 180 day stamp. The people that insist on an extension are then given difficult lists of requirements that change each time they return with everything.
First of all, the non-O visa IS the retirement visa. You would get an extension in Thailand, not the retirement visa because you would already have that.
Second of all, you are looking at the wrong visa. If it's asking for a letter from the BOI, then you are looking at the LTR visa and not the non-O visa.
Because you already have an active visa. You can't apply for a new visa while you have an active visa. And you can't cancel an active visa. So therefore you couldn't get a new DTV when you already have an active one.
because there is no direct answer. Every immigration office has their own policy. The only place that can answer you directly is YOUR immigration office.
I'd be willing to bet the number of people that have gotten an extension on DTV is under 100. Immigration offices DO NOT want to give these extensions. Many have made very difficult requirements to extend, and then when you meet them, they come up with a new one that you don't have the paperwork for. Then you go and get the new thing they asked for and when you get back to the office there's another new thing added. On and on until you give up and do a border bounce instead. Most of the immigration officers will straight up tell you to just do a border bounce.
As far as the specific requirements, each immigration office has their own. So no one can tell you something is or is not a requirement because there are over 70 provinces and each has their own immigration office. I know for example in Chiang Mai they require you to show 500,000 baht in a Thai bank account. But people on a DTV cannot open a bank account. Therefore most people would never be able to get an extension in Chiang Mai.
Their phones like they are using now. Most of the Thai accounts don't even come with internet banking as default and you had to go to the bank separately to request they set it up. I don't know a single Thai person that even has an online banking login.