Hey Rederator,
sorry for the late reply. I've been in Vietnam and didn't want to reply on my phone. How long have you been in Whistler for? My sister lived there for 3 years and was a manager at the Longhorn Tavern, you probably know her. Haha. Anyway
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How reliable is the Japan visa run situation?
Very reliable. AFAIK Candians (if you're Canadian) can get 6 month tourist visas on arrival (at least they could in 2003, you better double check it) but they have to request it otherwise they'll just be stamped with the 3 month. Boat from Busan to Fukuoka (Japan) is cheap and easy. You can get a 2 night hotel package for about $200, you can even just get the morning ferry over, chill in the terminal for a couple of hours and get the afternoon ferry back (which I did twice many years ago).
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Should I be able to sign a 6mo lease, then leave all my belongings in my apt, then do a visa run knowing I'll be able to get back in?
Getting back in, easy. 6 month lease, possibly a little more difficult. What's your budget and what kind of place are you looking for? 6 month lease is very unusual here, I was asking my girlfriend about it and she was saying that the super expensive brand new apartments will do it and also cheap, one room, semi furnished, studio apartments will do it. If you're looking for something in between it might take a little searching and finding someone who is desperate to rent out their apartment ASAP.
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With the key deposit, how do I actually pay it? I'll probably go through a Realtor. Will they accept a check from my US/Canadian bank?
I pay with a bank to bank transfer from my Korean account. Not sure how you will do it. With a 6 month lease I'm hoping you can find a place with no key money that will just accept 2 months rent upfront. I managed to find a place like this when I first came here and was on a tourist visa however I don't think the arrangement was very official.
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And I'll be staying in a hotel for ~week when I first get there, so I'll actually be leaving Korea ~week before my lease is up. Will I have any trouble getting my key money back before I leave the country?
Yes. Count on it (having trouble that is).
If you have an amicable land lord then you may be able to arrange something but I don't see it as especially likely. If I were you I would count on doing a second visa run (as I said earlier, it's cheap and fast) and giving your self a little bit of extra time at the end of the 6 months to make sort everything out.