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Flight question Yangon-Siem Reap-Chiang Mai

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Hi
I'm thinking of traveling from Yangon to Siem Reap to Chiang Mai. The flights involve BKK layovers and take a chunk out of the day. I looked at booking separate flights in and out of Bangkok. I can take Air Asia 9:30PM into Bangkok and spend the night at the airport -- I'm looking at a BA flight to SR early the next morning so I'd take shuttle or cab from DMK to BKK and spend night in an airport hotel. I think that means I'll have to go through immigration and check/uncheck bag more often, but the alternative is spend night in Yangon and my flight wouldn't arrive in SR until the afternoon. Similarly, I can fly late out of SR into BKK - then book a separate flight to CM. Does this make sense or is this unreasonable and too complicated? .
Thanks.

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