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how many time and money do i need?

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Im thinking about going in a trip next summer to asia for the first time.
I made 927347 different itineraries and the more i see the more i want, i guess that might happen to everyone. Since i have to pick and after i read a lot of forums, travel guidebooks and seeing TV series and documentaries about the zone i think i decided what i want for my first time.
I'll be traveling in and out thailand, then north in a night train as i think it would be a nice experience. I first looked at the mae song loop but as it will be rainy i decided i would leave that to another time. I would see Chiang mai for a couple of days and then i would take a slow boat to Luang prabang. Then go north for some trekking, going down to vang vieng and finally Vientiane. Then i want to to back to Bangkok, maybe by train. I would take a flight through Air asia so i skip all the border challenges to Phnom phen, take a bus to siem reap and go back to Bangkok. Is there a better itinerary between the places i want to go?
I'll be traveling cheap, hostels and eat locally. What time and how much money should i need to mais this jorney? I'll be going with my boyfriend.

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