Not sure if you have been to thailand before….if not then plan a short visit and travel to certain areas to get a feel for the different places and people….you will find that thailand stocks pretty much the same stuff you have in Canada….sheets,electronics and so much more…speak to people in thailand,ex pats,visa people etc…..then make your move….good luck,thailand is fabulous!
Everything is possible,you need to determine where in thailand you would like to live,check it out to get a feel for the place and then check out various property options available….and ask lots of questions from fellow expats about the ins and outs……but in theory very possible and do-able.
Try the 60 days tourist visa which you can extend to 90 days……once in thailand you can then decide whether you like thailand and what options you have…..things change all the time,as do the rules and regulations
Thailand without a doubt,better infrastructure,hospitals,airports,shopping centres etc…..and if you obey the rules,stay away from politics etc then you will find a piece of paradise to enjoy!