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@danwentskiing
Just finished my trip. Amazing country and generally very easy and safe for tourists.
Things I liked most:
Activities in general (rather than boozing) but especially a tour of rural sukhothai - the guide was amazing and it was great to chat directly about Thailand, the life of a rice farmer/whiskey distiller/furniture maker all day long. Scenery was great too.
Chiang mai - very touristy but much more comfortable than Bangkok
Overnight trains (they are slow and usually run late) but you basically have a bed (if you choose the lower bunk) and the views are great.
Stuff I was lukewarm about
Food. I expected this to be a major high point and it was generally good and cheap but I got food poisoning twice in the last week and it was only really amazing a few times. Admittedly my budget was low -£1-5 for a meal.
High season - if you can, avoid the Christmas/nye period. I never missed a bed but travelling between places by plane/train was often fully booked or unaffordable. Alternatively, book months in advance but then you will lose the spontanaiety
Islands (this was maybe season rather than anything). I got scammed a few times on taxis that didn't show up and accommodation. I went to over-developed places though (Samui and Phuket)
I'd definitely come back but I would do a few things differently and trust my instinct on food a bit more (would've avoided food poisoning this way)