Do I need to make any preparations for my trip to Chiang Mai, or can I just land and get a visa exemption?

If you know you're staying more than 30 days, I recommend you get a single entry tourist visa (gets you a 60 day stamp on entry) at the Thai consulate in Toronto or Vancouver. It would be cheaper than a 30 day extension and you don't have to spend half a day sitting in immigration.

If you're not in Toronto or Vancouver, it can be done by xpresspost mail... give it 1 week turnaround. Go to their website for the form and all the info you need to apply. Note, the Toronto consulate require an official passport size photo with the stamp on the back indicating when it was taken by the photo shop.

Some airlines can be picky if you have a one-way ticket and want proof of onward travel or a visa. If you have a return ticket, they won't bat an eye.

Yes your ok and don’t forget your cash

a significant percent are required to have proof of onward travel before boarding if u have a 1 way ticket or your return ticket date is later than your 30 day stamp ..several ways to deal with that ..also the equivalent of 10 or 20,000thb cash in pocket which is not a bad idea for any traveller to have some cash

FYI if you choose to stay longer you can fly to Perth Australia and apply for the 6 month METV for $200...it’s the only Thai consulate around that sells it to non permanent residents or citizens...

Your airline might ask for proof of outbound travel. I have been able to sign a waiver whenever asked but I’m sure that there will be a time that I have to actually produce a ticket.

Correct, not sure about the $60, it is 1.900 Thb.