Hi
Accommodation.
Sometimes when a place claims 2.5 stars its not usually any higher and you may find it a bit lower than what they actually claim it to be. Places charging $50 or less a night are not going to provide much more than clean (hopefully) and generally, basic accommodation with breakfast. Some friends have stayed in City Lodge and found it quite ok for the price. (clean and handy to Skytrain, shops restaurants etc). They travel a fair bit so I respect their opinion. Have a look at some of the reviews on other forums such as Tripadvisor and form your own view. Generally you will find a couple of negative posts when people review places but weigh these up against the majority before deciding.
How much money needed for food?
Well, how long is a piece of string? Depends how hungry you are - what you like to eat, basic food or high end and where you want to eat. I think you can get by quite nicely for $10-$12 a day if you eat in the food halls or on the street and you are on a tight budget. If your preference is to eat a bit more upmarket allow yourself $20-$30 a day and you will eat well. (Have a look at my recent review on Suda if you stay at City Lodge, its close by and you will eat well there quite cheaply- around $3-$5 for a dish) You can really spend as much as you want. There are plenty of places where you can spend $100 easily on a meal if you wish.
Travelling
You can do the booking from your home base if that makes you more comfortable or you can do it yourself on the internet or choose a travel agency in BKK- plenty to chose from. Trains to Chaing Mai are popular so don't leave it to the last minute. Planes are easy to Phuket. Depends where you are when you want to get to Phi Phi- there may be some bus travel required before you catch your ferry to the island- a local travel agent can help you with this- travel is easy in Thailand.
Silk Cloth
Jim Thompson fabric is well regarded and its expensive, but good. They have a factiory outlet on Soi 93 Sukhumvit or you could visit the Jim Thompson House where they have a retail shop. (There are also shops in the 5 star hotels in BKK) Its opposite National Stadium, Rama 1 Road Pathumwan in BKK. You can catch a Skytrain there. There are lesser quality(but quite ok) silks available in places like MBK shopping centre.
Hope this helps.
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