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Okay, a couple more questions:
How is the TV over there? Can you get any western shows? Do they have SKY? In the cheaper hotels you described, do they even have TV's?
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I have a satellite package from UBC and it is decent. CNN international, BBC, Star Movies, HBO Asia etc. Also get shows like Survivor, Fear factor, Alias, 24, Lost, 4 sports channels (a lot of soccer). Here's a link to UBC Thailand:
http://www.ubctv.com
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Also, let's say I decided to take your advice and just fly there and play it by ear - what's the best way to find a cheap hotel for the first few nights?
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I would book something online first. At least for the first night. That way you can go there direct from the airport and not have to worry about it. I haven't booked using this site before but maybe others can comment on this.
http://www.hotelthailand.com