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Hello, I have asked a friend who has had the experience of entering Japan on multiple consecutive tourist visas over the years, and this is his reply:

About your question on tourist visas---
My approach with borders and immigration guys is to offer as little as possible except for smiles and nods. I would not advise telling them anything about houses or plans for long term stays. There are a number of things that you are permitted to do on Temporary Permission to Stay (aka tourist visa or in many cases, visa waiver), but living in your own house in Japan is probably not one! The Immigration department has an English site that lays it all out. If your friends are planning on doing this for years, it's probably best to study the permitted activities and maybe mix them up. I just said "tourism" each time when asked. Once or twice I said I had not been to Hokkaido (or Okinawa or Kyushu) and wanted to go. I was ready to say I had gotten ill on the last trip so was not able to do what I wanted, but it was never necessary.

I was never refused entry, but I was once told that if I tried a quick exit and entry when the 90 days I was being given right then were over, I would be denied entry. So they gave warning. I think I was coming in for a 4th in a row, they said that I had to stay out for 90 days a year. (90 days is the standard for a Temporary aka Tourist stay for the richer countries.) So then I was staying 9 months in and 3 months out. After one or to years of that, they said I had to stay out for 6 months/year. I never asked if the determining factor was entries or time actually spent in country.

Nobody remarked on anything when I adhered to the guidance I had been given, and had at least 10 days or 2 weeks for my short trips between entries. Lots of interest, however, when I went to Seoul on a Sunday and came back on the Tuesday! Even though it was only my second entry in that year, 3 officials went fairly apoplectic. In an agitated manner, one said, "You cannot work!" Poor guys, they are obviously bound by whatever guidance they are provided, and maybe nobody thought of such cases. One guy searched 2 different computers two times each and finally sheepishly gave me the stamp and let me go. I thought it was interesting that the original guy on the desk on the line asked almost incredulously, "You are traveling alone!? Where are your friends?"  ha ha ha. Suspicious traveler!

I hope this helps.

Thanks tokyovoice, that was a very helpful reply!  It does kind of confirm what I have heard a few times re immigration getting difficult with multiple in and outs on 90 day tourist visas.  Yes, I can see they would have concerns re working illegally....but we would be obviously beyond that stage - or even interest. In fact, already am - LOL...
I've also been digging into issues like transportation (can I buy a car there as non-resident - answer is: essentially it is impossible - unless it is going to be shipped out of the country immediately).  Another issue is long-term travel insurance which I would buy here in Australia.  Not cheap and length of coverage is an issue I'm still working on - searching for a compatible company.  So while still interested, I can see it's going to be harder and more expensive than I thought.  We may be forced to continue on the AirBNB routine and rental cars for shorter periods.  Thanks again for taking the time and trouble to send such a concise reply.  It did add a lot of focus, and considerations.  Cheers!

Hello Charles,

Glad I could be of some help.  When you do AirBnB, do you rent full apartments, or do you share with the owners?  I'm just curious, because we live in Tokyo and my daughters have gone off to boarding school in Penang, Malaysia, so we have a room that we are planning to rent out semi-longterm.  In other words, the whole apartment would be shared with the two of us.  If you lived in Tokyo, you wouldn't need a car, and we're in Osaki, right on the Yamanote line.  It's fully furnished and the apartment is very spacious and on the ground floor.  If you were to come and go for 6-9 months a year, we could be flexible and guarantee the room for you again whenever you came back.  Fully furnished, no key money or deposit, just first & last month's rent, utilities and cleaning included.  ¥98,000/month for a Japanese-style 8-tatami room, private toilet, shared bath, kitchen, living/dining.  The apartment is 115 square metres and 6 mins walk to the station.  Free use of bicycles.

If you have any interest in Penang or Kuala Lumpur, I also have apartments there that are fully furnished and currently vacant.  If you're interested in either of these places, please let me know.
Cheers!

Hello again, Charles,

With regards to your question about buying a car in Japan, I think it would be difficult if you didn't have residence cards, i.e. longer-stay visas.  The other thing is, as far as I know, you are only permitted to buy a car if you can prove that you have an official parking space; you need to go to the police station with proof and they give you some kind of authorization that you then show to the car dealer before the sale can go through.  Finally, don't forget that you need to have your car certified every two years in Japan, which is a costly process.  My friend in Tokyo does some kind of share-hire, where she can rent a car for a few hours, or part of a day on a weekend and it's very reasonable.  If you are going to be coming and going frequently on tourist visas, you can buy Japan rail passes each time you come in and use them to get around.  Huge savings there.  If you decided to take me up on my offer of accommodation in Tokyo, we are just one stop from Shinagawa, where you can catch the shinkansen, and only 25 minutes to Haneda airport, which has a lot of low-cost and international flights, so using our place as a base to explore Japan would be ideal.  There's also a great onsen just a 10-minute bike ride from our house.

Again, I hope this helps.