The issue I can see would be boarding the flight in the first place. If the return flight is more than 30 days after departure, check in staff would want to see either a visa, or a ticket out of Thailand before 30 days.
You don’t need a flight out of the country with a visa in your passport in order to board the flight from the UK. If the extension of stay whilst in Thailand is your plan, then stick to that plan. If you want to explore the possibilities of getting a one year O-A visa then that’s a whole different thing. I know the London embassy like to point people in that direction, but I always think that it’s best to make your own plans/decisions. The costs, and time taken to get the police reports and medical are not insignificant. Worth finding out, but if you’ve already researched getting an extension when you arrive in Thailand and decided that that’s what you want to do then just stick with that plan.
Just show the check in staff at the airport that you have a visa and you’ll be fine boarding the plane.
I think it's possible, but I'm not sure what kind of visa you would normally get for doing that. As I said before, my experience of researching this kind of thing was to be with a work permit, and a visa related to being married to a Thai national which gives different results. You would need to contact a law firm that has experience of setting up companies for foreigners and all the visa requirements that that entails. Quite a few Thai law firms don't have that experience, so shopping around is strongly advised. Most of the specialists are more likely to be Bangkok based than up country. The one I spoke with was confident of their firm's ability to deal with immigration in Chiang Rai for me (until everything fell to pieces, as it often does!)
There are, obviously, law firms in Chiang Rai, but I wasn't all that confident in their experience of dealing with foreigners setting up Thai companies.
I think the only option you have is to be a director of the company that owns, or runs the bar. The company wound need to be properly set up, have registered capital, and registration documents. Then you might be able to generate all the necessary paperwork to get the visa you want. I say might, because I’m only familiar with how that works when the person wants a work permit, and you say you don’t. You most likely wouldn’t get one for running a bar anyway.
I’m not sure if you’d get a years non b though. You might just get 90 days.
You’d need a law firm to set the company up so you could ask them for more details. But I think setting up a company is the way to achieve what you want.