Getting a job in Thailand is not easy, although you may be able to teach if you have the ESL qualifications.
An alternative might be to get an education visa to study here. There are many universities that have programs in English.

Tourists are limited in the length of time they can stay and the number of times they can renew a tourist visa.

While the cost of living numbers in Bangkok from that web site you provided are ballpark, actual costs will depend on your lifestyle. If you are willing to live in a one room apartment with built-in bathroom, rent might cost about US$100 or less.
Retirement: If you get a non-immigrant visa from the nearest Thai Embassy or consulate, you can apply for an extension of stay for a year at a time as retired. This requires putting the equivalent of Thai Baht 800,000 (about US$25,800 @31 baht to the US dollar) in the bank each year at least 3 months before you apply to extend the extension of stay. If your retirement funds are in the form of a pension, you need to prove that you get at least the equivalent of Thai Baht 65,000 per month (about US$2100). Or you need a combination of a pension and money in the bank that total B800,000 per year. For example if your pension is $1000 per month, multiply it by 12 and then subtract that amount ($12000) from the equivalent of 80,000 baht which leaves $13,800 that you have to deposit in the bank here annually in baht .

I cannot compare Chiang Mai to Bangkok as I have not been to the former in many years.

Foreigners are not allowed to buy property in Thailand, but you can buy a condo. As for houses and apartments buildings, they must be owned by Thai citizens. So renting out rooms is probably not an option unless you have a corporation with Thais controlling the shares. I strongly recommend that you not jump into any investment deals until you know the country and the people. It is easy to get ripped off.
I am not sure what a PR visa is. It is easy to get a tourist visa, but as I noted above there are limitations.
- Are they tax / expat friendly? If all your income is from abroad, you do not need to pay any taxes here, as there is a treaty between the USA and Thailand. If you get earned income from within Thailand the rates can be quite high, and because expats are expected to earn a certain amount, As far as being expat friendly, as long as you do not interfere in their affairs, the Thai can be friendly after they get to know you, but are usually shy at first.
- Low crime. Expats are generally not targeted and left alone, unless the expat goes looking for trouble, in which case they can get it returned many fold. Generally speaking it is very safe in Thailand, but one must learn the exceptions, which include the 3 southernmost provinces of Thailand, where Muslim "separatists" (aka bandits) do tend to create havoc, murdering and robbing.
- Affordable and good quality medical care?. Many of the doctors have been trained abroad, but there is currently a shortage of nurses, and there is definitely a shortage of nurses with skills in other languages. BUPA Blue Cross and some other companies offer health insurance here, but if you have a plan in the US, you might check to see if you can be covered in Thailand.
Weather: Thailand is a tropical country, where it rarely gets below about 80F, and because it is a tropical climate it is humid. Chiang Mai can get a bit cold in the cool season November through February), particularly in the mountains, but at the same time4 the days can be quite hot. . In the hot season, Bangkok temperatures can exceed 100F. Thailand also has a lot of rain and in many areas there can be severe flooding. There is easy access to beaches and mountains (and forests), but not necessarily to all three in a single area. There are many beaches within an hour or three from Bangkok, but Chiang Mai is landlocked, as is most of the north. The beaches are mainly along the Gulf of Thailand in the Central and Southern parts of Thailand as well as along the Andaman Sea.,
Internet services depend on location. In Bangkok I get excellent service, but people in some of the up-country provinces in the north and northeast do not get the same level of service.

In cities like Bangkok and Chiang Mai there is excellent infrastructure, but it is not the USA, and do not expect Thailand to be like the USA. Learn to like it for its differences. Its culture is very different and the behavior of Thai people can almost said to be 180 degrees from the behavior of Americans, although these days, it is hard to define "American behavior". As Dorothy said in "The Wizard of Oz",
"Now I know this isn't Kansas". Culture shock is not uncommon among expats coming to Thailand for the first time, and even though you are Asian Canadian, each Asian country can be very different from its neighbors.
English friendly: There has been much improvement in this area in the past 40 odd years, and in Bangkok English has become common, and I suspect in Chiang Mai, as well. However in other areas of the country English speakers might not be readily available. But learning to spea, read and write Thai can be a lot of fun, as it is a language where the pun is appreciated, and the Thai do not get upset as we westerners butcher their language, or at least they will show appreciation that we are even trying to learn. In fact the Thai tend to be respectful towards other people, courteous, and tolerant, characteristics lacking in modern America but still prevalent in a predominately Buddhist country. If you decide to come here, let me know and I will PM my extensive list of Do's and Don't in Thailand.

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better to ask so many questions is to go and live there 3 or 4 times to feel if you agree this country, customs, culture and climate, and the people ...
you can choose other city like me; i need sea , seafood, like to visit parts of nature and move; i 've chosen prachup kiri khan and i bought land in coconut garden , 600m from the sea. between bangkok and south, close to birma and for cheapest price in south and good weather...but not too much foreigner...
you can rent 30 years , a land to built your own house.

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00abuse

Thank you for your replies, especially caughtintheact for so many details, which are exactly what I wanted to know. I really appreciate that.

I think to have to put US$25,800 -ish a year in the bank for getting an extension of stay is off-putting, and in my own opinion, not all that inexpensive at all. If I have to come up with that much money each year, I can just stay in N. America and won;t even cost me that much for the way I live. So it doesn;t make any money sense to move there now that I know how they operate. Thanks so much for the input.

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You might have misunderstood my comments. Just for clarification, you do not have to leave the entire $25,800 in the bank all year. It is not a security deposit, rather it is your expense money for the year, or at least part of it. It is about $2150/month. You can spend part of it or all of it during the year, but each year a fresh $25,800 must be put in the bank to get an extension of stay for the purposes of retirement. However, if you have monthly retirement income, like a pension, as well as funds in the bank, you can reduce (offset) the amount required in the bank as I explained before.

For example, if you have a monthly pension of $1000, the amount required to be put in the bank to get an extension of stay for the purpose of retirement is 25,800-(1000*12)=$13,800.

If you have a monthly pension, and it is at least the equivalent of 65,000 baht per month (about $2,160) you do not need to show any money in the bank; just be able to show that you have the monthly pension, the amount and that it is from a legitimate source.

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To make sure we're on the same page, in Year 1, I put in $25,800 in the bank, and used $10,000 in this year altogether. In Year 2, I'll have to put in $10,000 to make it a total of $25,800 again so I can show it to Uncle Thai that I still have $25,800 in my bank account for me to burn in year 2 so they'll grant me another year of stay in the country. Am I correct?

With your words,

"each year a fresh $25,800 must be put in the bank to get an extension of stay for the purposes of retirement."

, it could mean regardless how much I have left at the end of Year 1, I'll need to add a another fresh set of $25,800 to the bank account.

Another question is: does this rule apply only to retirees? I'm not at retirement age yet, so I don't know if this applies to me.

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Up to now I have only talked about extensions of stay for retirement. The objective of the Thai government is to be as certain as possible that you have a minimum of $25,800 in funds annually, because someone has decided that a foreigner who is retired here needs a minimum of $25,800 per year. For whatever reason, the government does not want foreigners running out of money here. If you will have no monthly pension, then each year you must transfer $25,800 here, regardless of the amount remaining from the previous year. Foreigners on an extension of stay for retirement are not allowed to work in Thailand You can have a business outside the country, but you cannot earn income here.

So you cannot just top off the remaining funds at the end of the year. If you still have doubts about how the system works, check with the nearest Thai consulate or Embassy. In addition I believe that you must transfer the fresh $25,900 3 months before your extension of stay expires. Retirement is not the only way to stay here, as there are other ways to enter Thailand and stay here, such as for education, to enter a monastery, as a dependent of a Thai citizen (if you are married to one).
There is more information at http://www.immigration.go.th/nov2004/en/base.php

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When I applied I went the monthly income route. All I had to do was visit the U.S. consulate in Chiang Mai, sign an affidavit stating that I received the equivalent of 65,000 baht per month and take it to the Thai immigration office. As I understood it, U.S. citizens were the only people allowed to do that. No documentation of proof was required by the U.S. or Thai governments. Of course this was 10 years or more ago, so that option may no longer exist.

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When I applied I went the monthly income route. All I had to do was visit the U.S. consulate in Chiang Mai, sign an affidavit stating that I received the equivalent of 65,000 baht per month and take it to the Thai immigration office. As I understood it, U.S. citizens were the only people allowed to do that. No documentation of proof was required by the U.S. or Thai governments. Of course this was 10 years or more ago, so that option may no longer exist.

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What you have to do on the first application for an extension of stay for retirement may vary from immigration office to immigration office, as even with the affidavit from the Amemb you might need to show immigration the proof of pension the first time.
Your experience in Chiangmai 10 years ago is similar to my experience at the American Embassy last year in Bangkok as far as the pension affidavit is concerned But in Bangkok it is now mandatory to make an appointment online at the American Embassy web site http://bangkok.usembassy.gov/acsappointment.html . It is a pretty simple process, and getting service when you have an appointment is saving citizens many hours. I do not know abouyt the procedures in Chiangmai.

I also recommend that anyone trying to renew their extension of stay for retirement purposes should check at their nearest immigration office about a month before applying to be sure the requirements have not changed. For example in some years a local medical certificate was required for a couple of years, then that requirement was dropped. At another time a map to one's local residence was required each time, and then dropped, but not at all immigration offices. At the forums of www.thaivisa.com there are usually fresh reports of experiences getting extensions of stay and the requirements. But there is a lot of noise on that forum, so don't believe everything that everyone says.

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