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How to make best of Thailand during Jul?????

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Hi everyone!
I am new to this site and joined it recently to seek advises from experienced travelers. I will be in Thailand during Jul 13 to attend a conference / seminar. My official stay is for few days only but I intend to take along my family (wife and two daughters) as we have never been to this part of the world and may never visit Thailand again. After some research I am horrified to know that Jul will be very difficult from traveling point of view but I have no other choice.
I have worked out simple schedule:-
1. Arrive Bangkok (The Riverside Bangkok)
2. 4 nights stay in Bangkok
3. 3 nights stay in Chiang Mai
4. 3 nights stay in Koh Samui / Koh Tao
5. 3 nights stay in Bangkok (Littlest Guesthouse)
6. Fly back to NYC

I have following queries to ask:-
1. I need advise for hotel / specialty lodge for Chiang Mai. It must not be expensive but located at a place from where I can enjoy Chiang Mai's scenic beauty.
2. I have not made decision to either visit Koh Samui or Tao or some other island. I want to stay in an island that is beautiful as well as quiet. I am looking for scenic beauty that surrounds Koh Phi Phi island. Can I get that type of beauty on any island in the East?
3. Which part of the year is better from weather point of view? Late June or mid Jul? As I have option to select any one of the period.
4. How best to fight bad / humid weather? Any good tips? What clothing (and how many) must be taken along?
This is my first set of questions. I will continue to bother all of you.

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