What should I consider when applying for a third tourist visa to Thailand after multiple extensions and border runs?

Tod Daniels, the rules there are a little different than other locations. For example, if you hold a Canadian passport you do not need to submit financial docs or have a round trip ticket. However, if you are a Canadian resident but do not hold a Canadian passport, these items are required. I did this two months ago so I can confirm this is the case.

@Ange *******

a single entry tourist visa is walk in the part compared to a 6 month METV.

If you find a consulate that's 'lax with the requirements' please post it ;)

what consulate did you apply for the 6 month METV in Canada that has no financial requirements? This is right off the thai consulate in Vancouver's website;

@Tod ********

okay

you definitely have to be out of the country to get a WP3 but you don't necessarily need to get a 90 day Non-B in another country. Many companies can provide you documentation to get a 90 day Non-B from the immigration office if you hold a tourist visa or a 30 day visa exempt entry.

Ange Morris You can still be asked to provide the 'proof ofs'. Around the beginning of last year, a friend of mine did a similar thing. He had a bit of history, but had been home to Australia and applied for a METV (no problem with that). He arrived in Bangkok, stayed 60 days, extended 30 days, then did a run to Cambodia to activate a second 60 days. He was refused entry at the border and had to either fly back in or fly to Laos and cross that border (can't remember which, but he was defo refused). Just be aware it's not a golden ticket... Be careful where you go to activate another 60 days. Vientiane, Laos still seems to be most user friendly. Also, carry proof of address in Thai, some sort of onward flight, and 20,000b cash in whatever currency as they do occasionally ask. Even with that it's all down to the IO discretion and if they feel like it, they can make things difficult for you.