I'm not quite what you'd call an older guy yet - I'm 32 years old - but I've been based primarily in Thailand for going on 6 years now.
I recently came back from a 10 day trip to Saigon, Vietnam and a beach town called Hoi An - and while it was a pretty cool trip overall and Vietnam is a crazy scene - I felt a wave of happiness wash right over me as soon as I stepped back onto Thai soil. It happens every time...
I also wholeheartedly agree with OP that the overarching atmosphere in Thailand is something of a "live and let live" approach to life. It's probably the reason that a lot of Western expats feel so at home here, myself included, and all of the hullabaloo about Thai xenophobia notwithstanding. In the States, where I'm from, there's certainly a lot of lip service to the IDEAS of freedom, but less and less of it is evident in the actual day to day reality.
One famous libertarian economist quipped that all countries and their governments are corrupt but the ones that should really frighten you are the ones with the money and resources to effectively meddle in your life.
It seems to me that you can bribe your way out of most petty troubles like not having a helmet on when you're driving a motorbike, or even something more serious like getting caught with drugs (although I wouldn't recommend trying your luck with that one). By and large my experience as a foreigner is that the police are interested primarily in making some cash; they're not on some giant collective power trip like they are in the US. Or at least to nowhere the same degree.
The practical consequence of all of this is that you're pretty much free to do what you want as long as you don't fuck with anybody, and nobody will bug you for the most part.
A lot of this is also attributable to the unique confluence of Thai religion, history, temperament, and culture. Of all of the countries in the SEA region I find Thais to be the most pleasant, all things considered. They smile a lot, they're warm and friendly, and generally helpful. Sure, the smiles are put on; sure they lie through their teeth about all things great and small. But a lot of them are genuine too, especially if you can speak a bit more Thai than the average farang.
I actually had a chuckle about this earlier today because I just got back from Vietnam and was thinking that the people there seemed more bellicose (got cursed at twice in the span of a week, which has only happened once in Thailand in 6 years) and less prone to "causeless" smiling, which is also something that will make people in the Eastern bloc countries think you're mentally ill (or so I'm told).
A Ukrainian friend of mine told me that Vietnamese are closer to Ukrainians in disposition than Thais. Hmm.
On the other hand, if you invert the perspective, why would you want to go around with a dour puss on, all morose and forbidding, eschewing the opportunity and tiny pleasure of greeting your fellow man with a small contraction of your facial musculature?
This is something I can appreciate about the US. People are really friendly and chummy with one another, at least in my southern home town in Florida. I'm not super smiley but it feels good when people around you are making an effort to interact warmly with one another, even if it's sometimes faked.
On OP's point about Thais not gossiping, my experience has been that they ask you probing personal questions about everything from your paramours to your finances, if you could call that gossip. Both of these really used to piss me off when I arrived here. But the Humphrey Bogart act and telling people to mind their own business won't endear you to anyone here, so I've learned to smile and deflect questions of that nature.
But gossiping I don't so much mind. So everybody in your neighborhood knows you bang lots of chicks. Big freaking deal.
The main point, as many have echoed, is that you can live your gossip worthy or non-gossip worthy life, whichever you prefer, without anybody actually interfering much into it. And that there is the rub.
Also agreed that with Thailand you trade several large inconveniences in the West with a plethora of smaller inconveniences. With perhaps the exception of sorting your visa situation here, which is a constant pain in the ass. And even that can be handled if you have 15 grand lying around by purchasing a Thailand Elite visa, which a friend of mine has and considers one of the best investments he's ever made. With the elite visa, all your immigration headaches disappear for the next 5 years.
The main inconveniences here are variations on the theme of lack of standards. In the West we consider doing things right and well the standard. In Thailand they consider doing things the standard. So like somebody mentioned, if you get electrical wiring done in your house, it's going to get done wrong almost guaranteed. Thais are half assers unless they're making papaya salad. I think this is really just an education issue because the younger Thai generation are creating startups, traveling abroad to study, opening all sorts of cool hipster businesses with an artisan bent, and are generally more switched on the necessity and beauty and purposefulness of doing things and, as long as you're doing them, doing them as best you can.
In terms of having Western amenities, you totally can if you're willing and able to pay for it. And even though Thailand has become more expensive - especially the gentrifying areas of Bangkok - it's still very affordable compared to the West.
Healthcare is inexpensive and top notch, although you need to do your homework and grill your doctors as you would anywhere. Many doctors are Western trained and speak excellent English, and the bigger hospitals have excellent diagnostic resources, lab facilities, and many specialists and sub-specialists. If you go to Bumrungrad hospital in Bangkok you'll see that it's filled to the rafters with Saudis and sundry Arabs who come here for medical tourism and the treatment of various genetic disorders no doubt caused by generations of inbreeding.
As far as street food being unhealthy - yes, it is. But why the hell are you eating that crap to begin with? All of the big cities have excellent hipster markets with lots or organic and local foods. Villa market and Tops in Bangkok and Phuket, and Rimping market in Chiang Mai. You can also order totally organic, wild, free range, etc., prepared meals and frozen meats / fruits / veggies direct to your door from PaleoRobbie nation wide, delivered in a styrofoam box on dry ice. You absolutely do NOT have to eat crap in Thailand, and you can always ask for no MSG and no sugar. Plus, some street food is awesome like the little baked sweet potatoes in the plastic bag that's leaching loads of BPAs most likely. ^_^
The nature in Thailand is also super stunning. I lived in Bangkok for almost 2 years and now I would never live there or any other big city for more than a few months of the year because they don't have nature. And nature is medicine. In Phuket or Chiang Mai or Samui you can go to the beach or the mountains every day. You can go swim in waterfalls and trek in the jungle barefoot on acid if the mood should strike you. Makes a HUGe difference in your well being.
The rainy season is definitely a drag because it's wet as fuck all the time, and you can't really go anywhere because roads are slippery and the beach / mountains aren't super appealing when it's pouring down rain. A good option during rainy season is to go to Bali which has a sort of inverse seasonal relationship to Thailand. That's if you want to stay in Asia. More on that in a minute.
As far as the women go, I've thought about this point too. Every country has a large population of less educated bumpkins and quasi-bumpkins, and a relatively small percentage of more cultured, sophisticated and educated people. Thailand is no different. But there are relatively fewer people who would fit into the average western milieux in terms of overall education and worldliness. And there are indeed very few women whom you can connect with on any kind of deeper level.
I'm conflicted on this point because my deep, philosophical needs are met by my male friends (mostly expats, and mostly training partners in jiu jitsu or fellow online business peeps). So I don't feel the need for my women to be on this level. Yet once the honeymoon period bangathon wanes and you realize you're with a puerile twit you might start to crave a bit more intellectual stimulation.
If you're looking for a wife then that's a different matter and not something I can speak on with any authority. I suck at even keeping a steady girlfriend. But the point is that if you share this sense of compartmentalization you can act it out in Thailand because there are plenty of chicks who will assume a fairly rigid partner role without expecting any "deeper philosophical" component. You be the man, they'll be the woman, and that's where it can stay.
*In terms of Thailand starting to wear on you after a while:
The modus operandi that I'm slowly transitioning to now is to spend 6 months of the year in Thailand to be used for training, resting, relaxing, and creating. And 6 months abroad in a more cultured country to hone business skills, music skills, stoke intellectual fires, and do intense periods of productive work. The lack of culture (classical music in particular) and easy lifestyle breed complacency and a sense of intellectual stagnation that have been plaguing me and that I don't intend to abide any longer.
But all things considered, Thailand is truly a wonderful place with wonderful people, nature and culture. If you can take ownership of the negatives and avoid / mitigate them as much as is in your power (a lot of which is simply proportional to your financial power) then you might come here and never want to leave. I for one will always consider this my home base.
??