Having been living and working in Thailand isn't an issue but cancel your work permit and extension before you leave Thailand. Have you maintained income from your UK company while in Thailand or is this a new company? A new company doesn't rule out a Workation DTV but without history you are going to have to explain how you will get income, if you have any contracts that would definitely help
If your licence has been expired for longer than 12 months I believe you have to start over again so you will either have to take all the tests or convert from your home license and IDP. So you will only get a 2 year licence
If you apply with a 1 month course there's a very good chance you will just be issued with a tourist visa as that is more than sufficient for the course you are applying for, rather than being rejected. If you want the DTV make sure your course is at least 6 months, preferably longer
You may have an issue with your joint bank account. All immigration offices inside Thailand view the funds in a joint account as belonging to each account holder, so only half the funds are yours. How the consulate you plan to use will view it I don't know, but you should find out before applying
the requirements handout from my office clearly states they want to see the money 3 months prior for all but the 1st extension which is 2 months. Saying that I don't think I've ever met the 3 months requirement and always got my extension albeit they've had long chats with the supervisor before approving. I've never had to interject, they just sort it out amongst themselves. Every year they say "next year 3 months".