The only official in Phuket that can sign the residence certificates is at Phuket Town. That's why the price there is 500 baht and you can get it back same day. For Blue Tree, you're paying an extra 500 baht because they have to drive the paperwork to Phuket Town, and that's also why you have to wait to get it the next day.
20,000 baht is the amount of cash a tourist can be required to show to enter Thailand. It's not relevant to a marriage visa at all.
To get the marriage visa from your embassy, you need to check what their requirements are. It will be a local equivalent to 400,000 baht in your local currency. Generally the only requirement is that you can show a bank statement (in your name only) with the amount of money. Some embassies MIGHT accept a joint bank account, but you would need to show double the required amount since only 50% of the money is yours. An IRA account would not qualify.
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.