BritTim

I believe you will most likely be OK flying in to Chiang Mai, an airport that has historically been less strict on visa exemptions. It seems that most of your periods in Thailand have been of limited duration, and there are significant periods in between. You do not fit the profile of someone who might be an illegal worker, the main category Immigration are concerned about.

The normal basic steps required (assuming he does not use an agent) are: Open a Thai bank account (if not already done so) and deposit 800,000 baht with proof it came from abroad. With at least 15 days left on his existing permission to stay, apply for a change of visa status at Immigration, based on retirement. This is taken under consideration, with a report back date about 30 days later. On the report back date, receive a Non O visa (immediately stamped used) and a 90-day permission to stay. Note that, sometimes, the paperwork for the under consideration period is incomplete on the report back date, and you must return later. Towards the end of the 90-day permission to stay (you are usually allowed to apply somewhere between 30 and 45 days early) you apply for and receive a 12-month extension.. As he is a Danish citizen, as an alternative to the 800,000 baht in a Thai bank account, he should be able to get an income letter from the Danish embassy in Bangkok that states that he earns a minimum of 65,000 baht per month in income. More details on the visa status change (typically called "conversion") and annual extension of stay is available in many previous threads.

That is important information. Are they only strict on tourist visas? It it possible to give guidelines on when you are likely to be denied?

If they are not already doing so, they will apply for tourist visas in Penang or Savannakhet. The queues there on certain days are already completely out of hand. They are set to get worse.

Good decision

One point I have just remembered could be related to your experience. Quite a few years ago, Immigration's system added a feature where officials were alerted if you had received a significant number of visa exemptions (from memory five, but I might be wrong) over the years, and instructed to screen you more strictly as a genuine tourist. This was at the time when the Thai authorities were concerned about some foreigners working illegally using border bounces to stay indefinitely in Thailand. I am guessing that the alert most likely still appears.

You also need to add a bit of time for getting across the bridge which is done on a shuttle bus. Also, applying for the Laos visa-on-arrival is usually fast, but add a little time for that if you do not have an eVisa. If you plan on using taxis to and from the border, allow about three hours. You can save money by using vans (certainly on the Thai side) but would need to add extra time. Perhaps, decide on taxi vs van on arrival in Nong Khai, based on how tight you are for time.

It is unlikely that they will harass an 80-year-old. Someone who is 49 will probably not be treated as a retiree.

As others have already posted, your OP is meaningless without more information, especially the land crossing used. The only thing that can be said for sure is that the Aranyaprathet/Poipet crossing has been involved in an ongoing "crackdown" for the last six years or so.

Nobody is going to assure you that all will be OK. Your chances would be better than 50% for sure, but there is a real risk of a denied entry. Be sensible. Fly to Vientiane, return via the Friendship Bridge, and fly back from Udon airport.

Probably, the stamp will be ignored when you apply for a visa at a consulate. There is a small risk that the wrong official could take it into consideration. Unknowable.

There can be many reasons. If living in some parts of Northern Thailand, a border bounce at Mae Sot or Mae Sai costs only US$10.

Although I absolutely do not recommend it, the cheapest way of getting from Pattaya to the border at Aranyaprathet/Poi Pet is by train (Pattaya to Chachoengsao in the afternoon, connecting with the train out of Bangkok heading to Aran). It is even cheaper than using the casino bus. To the OP: there is a high probability you are going to stuff this up. If you do not already have the 30-day extension of your tourist entry, do that first. Do not use Poi Pet for your border bounce unless you are a wild gambler. That crossing is known to hate those doing border bounces, and they can find ways to really ruin your life. Unfortunately, the other border crossings are not easy to do independently as a casual traveller. Leave very early in the morning. You need to take the bus from Pattaya to Chanthaburi and take a van or songtaeo from there to the border at Ban Pakard. Check the current location of vans and songtaeos when you arrive in Chanthaburi. As a naïve, inexperienced traveller, you will get scammed at Ban Pakard, but may well remain oblivious to the fact.

Every Thai embassy/consulate has its own guidelines over granting tourist visas. A few years ago, Ho Chi Minh City (and Hanoi) were good places to apply, with at least two tourist visas provided without the slightest difficulty. They have become a lot stricter, and I am not sure how HCMC will react to an application for a second visa (especially back to back). At the current time, I think the best places to apply for tourist visas are Vientiane (requires appointment), Savannakhet (very busy on Mondays and Thursdays) and Yangon. Wherever you apply, the days of unlimited tourist visas on demand are over.

You have a lot of research to do. Forget the idea of a school. That is fiendishly difficult to set up. On a shop, you could be a part owner with your wife. However, getting a work permit has requirements that must be met (including, probably, having at least two of your wife's relatives on paper being on the payroll). Your work permit would have restrictions on what you are allowed to do. There is a list of applications restricted to Thais. One of these is "front shop sale". You need to talk to a good lawyer, but to get a cursory understanding take a look at https://www.thaiembassy.com/thailand/working-thailand.

Setting up and running your own company in Thailand is not for the faint hearted. Assuming you are not an American, you need expert legal advice on how to retain control while having the company be Thai majority owned on paper. A Thai owned company (on paper) can purchase property but, again, take expert advice on how to structure things. You are talking about a substantial financial outlay, and you had better have a very good business plan to justify it. Have you run your own company overseas in the past?

It is important to be totally clear and exact about what your mother actually possesses. A multiple entry Non O visa (only available from a few embassies/consulates) allows unlimited entries into Thailand until the expiry date of the visa. Each entry is for a period of 90 days. A Non O-A (long stay) is also multiple entry, allowing unlimited entries until the expiry date of the visa. However, it allows a full one-year stay each time from the date of entry. Neither of the above requires anything but the visa to enter. There are other kinds of visas, that might also be called retirement visas, that have their own conditions. If your mother received a Non O visa and one-year extension of stay from an immigration office in Thailand, the rules are different.

This is a good answer. It is entirely at the discretion of the local immigration office. If they allow the application, a retirement extension is usually completed the same day, or overnight at worst.

As others have stated, there are no immediate consequences for a one-day overstay when leaving by air through one of the Bangkok airports. My own view is that overstays of any kind should be avoided if possible. They do become part of your immigration record. The wrong official can decide to make an issue out of minor overstays in the future in situations where officials are called on to exercise discretion. For instance, a year later when seeking a visa exemption after significant time on Thailand, an official might refuse you a visa exempt entry with the overstay being a contributing factor. Not probable, but best avoided.

For future years, bear in mind that those visa exempt entries by land should be husbanded as your emergency entry method when you are unable to, for instance, get a visa from a consulate. A first tourist visa application in Savannakhet will definitely be no problem. Be aware that embassies/consulates vary in how strict they are when granting tourist visa applications. After you have spent over 180 days in Thailand consecutively as a tourist, some consulates may deny your application. Very commonly, less strict consulates will refuse your application if applying for your third tourist visa at that specific consulate. How long are you intending to stay in Thailand? Staying over six months requires some care. Staying a year requires a good appreciation of which embassies/consulates to use, and which airports might possibly be problematic for flying into, even with a tourist visa. Being a long stay tourist used to be feasible. These days, stretching it out longer than about 18 months requires care and some luck.

There is no definite answer to that question. It depends on the senior official at the labour department office. I would suggest visiting the Labour office to discuss your plans with them. If you develop a good rapport, rulings are much more likely to go in your favour.

The key points: You have a multiple entry Non O visa (based on marriage to a Thai) which you received in Savannakhet. It is valid until Dec 23, 2023 You intend to enter Thailand on or about Oct 4th. My impression is that you want to stay indefinitely. Consequently, close to the expiry of the permission to stay from the entry on Oct 4th, you plan to go to Savannakhet for a further multiple entry Non O visa, using this to continue staying in Thailand. I further assume you know that this will entail periodic border bounces. From somewhere, you seem to have developed the impression that there could be a problem with what you are planning. However, your intentions are straightforward and, assuming no changes in the rules between now and the end of 2023, everything should go smoothly. If you are still concerned, explain clearly the difficulty that you think you could run into.

Every 90 days, you must either travel outside Thailand, or apply for an automatic 90-day extension of your permission to stay (admittedly a pain).

Doing border bounces is a possible solution, certainly permitted across the Cambodian border. However, depending on where you reside in Thailand, a trip back to Cambodia every 14 days could be extremely inconvenient.

With a tourist visa, you would be fine entering via the Friendship Bridge at Nong Khai and at certain airports. Even with a visa, entering via either of the Bangkok airports, while you would probably be successful, would involve some risk. You really must avoid visa exempt entries for the time being, certainly through airports. If you absolutely must do a border bounce for a visa exempt entry, the risk is lowest at Mae Sot or Mae Sai, with most Laos crossings the next least likely to result in problems.