Paul, you can apply for either non O based on retirement or based on having a Thai wife. The retirement one requires double the funds the Thai wife does, 800k vs 400k but the retirement one requires less paperwork. I suggest you go to your local IO and get the requirements handout for both options and pick the one that suits you better. I easily qualify for the retirement option but I've always chosen to use the Thai wife option because that suits me better.
You won't be getting a Visa on arrival, you will get a visa exempt stamp, currently 60 days, but likely to go back to 30 days sometime soon, regardless which you get, it is extendable by 30 days at the IO for 1900 baht.
... not true, landscape or portrait is fine. I've always had a mixture of both and just did it again on Thursday. I also just print with normal colour printer onto standard A4 paper.
... it's not that difficult, you just have to time everything right switching from the 90 day to the 1yr extension. I had 1yr multi entries for years doing a rotation schedule up until covid when it wasn't available to return to Thailand. I've been on the 1yr extension ever since. For sure it's not ideal and inconvenient but it's definitely doable and only needs to be done once per year. Just make sure you get a multi entry permit.