Yes you would need to apply for a new visa. I do not think the Embassy or Consulate staff would have a problem with your explanation or even if you did not explain. Some years ago I had a single entry Thai visa which I did not use for reasons similar to you. It has only come up once. An immigration officer became confused when the number of visas in my passport did not equal the number in their database. After scratching his head for a bit the Officer asked if I had one I had not used. I said yes and all was well and I was on my way
I think you have already received good advice but I would just add, take a good luck at the enter before date on your visa. Any or all entries to Thailand will give you a 60 day stamp and could be extended at immigration.
I do not have any personal experience with Airbnb in Thailand but based on what I have read You are unlikely to get a TM30 from your host. Most Airbnb hosts in Thailand seem not to want anything to do with any govt agency so they do not have to pay tax on the income
I do not have any insider knowledge, but have a lifetime in IT. I am convinced that the core of the system is the e visa on arrival app that Thai immigration use. They extended it and presented it to Foreign Affairs without any significant consultation about business processes. As a result the Embassies and Consulates are just now taking the first baby steps toward actually using the system.
No two immigration officers or airline agents are the same but I think you will not have a problem as long as you have your story straight. I see Tod has also replied and always follow his advice. I am a lifelong IT guy and find it depressing to see that the pathetic e visa system is actually driving people away.
I have applied for several METV at the consulate in Vancouver. Like your friend I was looking for a fourish month stay. I do not specifically recall the application asking a return date but it likely did and if so I would have entered my actual return date. I have found the staff at the local consulate to be pretty chill. I do not think your friend will have a problem.
Cpletely normal for them to block your extension until the TM30 was fixed. 800 baht fine also legal but cruel in your case. With Mae Sai you have to figure they will be open 7 days a week because the border is open 7 days a week. I do not know exactly where you live but of you had gone to Chiang Rai office on Monday I think you would not have been fined.
I do not think you need to refile when you go to extend as long as the info they have on file is up-to-date i.e. passportatch, address match and TM6 departure card number match. If something is not right you will need to fix it and possibly pay a fine before they will give you the extension. As one of the other posters mentioned you might need to refile if you stay in a hotel for the weekend. If that hotel does file for you, that address would replace your permanent address and you would want to refile.
Thankfully the online has not reached Canada but I took a look at the documentation back in March because I was curious. What I saw looked like it was going to be a white hot mess. It sounds like you are living it now.
Biff, all correct info. The only thing I will add is that a day pass is the default. I believe you can ask for a pass that would give you a few nights stay but it would be just in Tachileik. I have also read that you can do some serious hoop jumping to be allowed to go to one other specific city if you have a local guide.