Hi Nicola,
I haven't done the round the world part yet, but I have hit a few countries on your list so I can offer up some advice on them at least.
First Thailand: as I have been there numerous times as my wife is from there so I know a lot on the subject. I definitely recommend going during Thailand's low/rainy season. You will save tons of money and despite being called rainy season, it really depends what region you are in as far as when the rainy season occurs. I've been there at various times of the year, it doesn't change much as far as the heat and rain except from November-March, that's the dryest and coolest, but most expensive. The rain generally won't totally interfere as it's normally short bursts of downpour most days, so for a short time you'll want to stay indoors, but it passes. Though there are some days that you'll be rained in, but you just find something indoors to do and it's all good. Get used to carrying an umbrella pretty much anywhere you go in southeast Asia. Women also use them there to keep the sun off of them when it's not raining. As far as traveling alone, don't sweat it. Just make sure you don't stray too far from the beaten path alone, you may meet a friend in your journey there, I went alone my first time and befriended many other travelers on my journey. As long as you're in the major tourist areas (Bangkok, Phuket, Samui, Chang Mai, etc...) you'll be just fine. If you find someone with the same agenda try to buddy up at least for the taxi trip to reduce the "alone appearance" of your travel. Honestly it's quite safe though, just make sure you use either the "taxi meter" (this is the name of the real taxi's labeled on all of the cars) or a tuk tuk, however the tuk tuk drivers generally will take you places you don't want to go as they get commissions from businesses such as restaurants or shops, so unless you want unscheduled stops, stick with the taxi meter company, they're generally easy to find anywhere in the cities. I do recommend that you have Thai translations of your destinations on paper to give to taxi drivers. You can easily use google to get those translations (lots of internet shops around to use very cheap), otherwise English-speaking concierge at the hotels will normally be willing to do this for you as well if you go the hotel route instead of hostels. Also you were asking about how to dress, if you plan on visiting any Thai temples, plan on wearing long pants as it is frowned upon for women to wear shorts or skirts in temples. I can give you any more info you'd like on this country, just send me a message if you want to know anything else. I have tons of info and recommendations on Thailand. FYI, if you go to the Northeast, you may want to consider crossing over to Vientianne, Laos for a day or 2, it's worth a look and very cheap.
Australia
I have only been once and for a short time, but made the most of what I could. Just remember that they are the exact opposite of us as far as seasons go, so our summer is their winter etc... However, you can definitely take advantage of going in their winter time to go to the northeast such as Cairns to see the Great Barrier Reef. You'll get amazing deals in Cairns and it's not cold at all, they are a tropical climate up there. I went in June, there was pretty much no one there, I had the beach and hotel mostly to myself, stayed in the city of Cairns and also ventured to Trinity Beach, it was all beautiful. Go see the reef while you still can. You can also go to check out the rain forest and village in Kuranda which is a short bus trip from Cairns. It's worth the trip doing the cable car going up the mountain was incredible and the train ride back down was great too! I was in Sydney and it was cold in June, so I didn't do as much as I would have liked, such as the harbor bridge climb or the famous Bondi Beach. There's still plenty to do as it wasn't exactly freezing, though I'm from Chicago so I am used to brutal cold winters compared to what they get there, I was walking around with no coat - just shirt and jeans and I was fine, but they were all bundled up in winter coats and hats as it was cold for them... not cold enough snow at that point though to give you an idea.
Hope all that helps. Email me if you have any other info you'd like on Thailand for sure, I'd be happy to help.
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