If you only have 9 months left on your passport when you go for the next extension you will still get an extension but only for the validity of your passport. It's better to renew your passport before going for the extension and then you will get the full 12 months. UK passport renewal in Thailand is straightforward , you use VFS Global to do it which has offices in bangkok and chiang mai but if you're not close to either you can use a service such as
They have got stricter on the medical treatment. Now you normally need a treatment plan of at least 6 months signed off by a recognised doctor on the official letterhead of the medical facility he works at.
If you don't have a full motorbike licence then you have to do the complete test in Thailand. The easiest is to sign up with a school who will take you through everything then just give you a bit of paper to take to the DLT to get your licence issued
For the statements if they meet the criteria just upload them again. For income it sounds like they are looking for you to show how you can support yourself for the 5 years the visa is valid for
Some immigration offices align your 90 day report with the visa but if they did you would have filed a 90 day report at the time and they would have put a slip with your next reporting date in the back of your passport
The first one on each entry can't be done online, but if you are organised you should be able to do by post or you can get someone else to report on your behalf