Would welcome feedback on challenges faced during extended stays.
I just passed my 3 year mark, leaving the country only for travel. Guess that qualifies as an extended stay. Don't know what you mean by 'challenge', so I'll use my definition. As an expat I consider things to be challenges when they're: 1) An unrelenting discomfort, 2) Takes too much time and effort to deal with even with careful, optimized planning, or 3) Makes one question if the presence of absence of something is enough to make them live elsewhere.
No #3s yet.
No #2s. I have plenty of time, know that patience is required and if the system wants to bat me around like a ping pong ball just to make me howl, I smile and don't give them the satisfaction.
I see real estate and housing issues as other's big #2s because they didn't know or didn't follow the first rule of buying / leasing real estate in a corrupt country: Only spend the money you can walk away from. Foreigners are murdered in Thailand because they didn't have the common sense to walk away over a real estate deal gone bad. Oh sure, there are contracts, laws, lawyers and judges. But in the case of the most recent incident here, there are also people who learn your patterns and smack you in the face with a wooden beam as you ride by on your motorbike. Best lawyer in town doesn't help if you spend the last year of your life in a coma.
#1s The concept of 'too loud' doesn't exist. From conversations to public announcements to rolling trains of advertising sound trucks, the Thais have never met an intrusive sound (except at some Buddhist facilities) Hilltop wats are great places for quiet time when I let the noise get to me. I just purchased some 'musicians earplugs' that cut louder sounds but still allow normal conversation. I'll find out how they work when the package from the US arrives.
The second #1 for me was both hard and easy to let go. Hard because I want to go postal on the people involved. Easy because I know that would be a Very Bad Thing. Imagine what would happen in the US if you parked a vehicle in a narrow urban alley, blocking it to all but foot traffic for 10 minutes. Ruckus would be raised, threats would be hurled, anger would abound, one's parentage would be questioned, etc. Here ... such behavior just another day in Thailand.
When Thais encounter behavior that would have the actor labeled as a major a$$h*le in the US it doesn't raise an eyebrow here. One can't tell from the Thais that anything is amiss. They wait quietly or change their path, change their plans, anything but show intolerance of others who are putting there wants first.
The third #3 is the nature of the other expats. 'Odds and Sods' as one Brit put it, meaning a motley assortment of odds and ends. (Hey, I resemble that remark.) The larger expat communities have enough interest groups (weekly softball in Chiang Mai!) not centered around alcohol. In the smaller towns, especially ones not noted for many Americans, finding guys to hang out with can mean a significant lowering of one's standards and tests one's tolerance.
Others discussed retirement visa. There are two. The official one is a Non-immigrant type O-A. Can only be obtained in the country that issued your passport. Harder to get, easier to live with. The unofficial one is a Non-Immigrant type O. Most expats have the latter.
kramer said of Chiang Mai "air quality becomes intolerable from about the beginning of March". Different folks have different ideas of intolerable. I took an apartment in Chiang Mai this last high season, arriving in late October and intending to stay until the end of Jan or when the air got bad. By the second week in Jan my eyes had a slow burn 24/7, so I returned to Hua Hin.