Hi,+ welcome,

By the time you get to the bottom of south america you should then have very good ideas of what to do next, so don't sweat too much at this stage about 'what to do next'.

Having said that ...
Don't skip africa ... the bottom bits are reasonably stable. I'd do that first ... because i think you'll find asia cheaper and you'll be more flush with funds earlier in your trip.
Again .. do factor in the shipping costs. They are a substantial part of the total.
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Singapore is expensive not due to the costs of shipping, but due to the costs of import/rego/insurance. Better to go to some other asian country .. with cheap shipping and then ride from there. Most people ship to Thailand?

Singapore is such a small place you can do it buy public transport and save a lot of cost/paperwork.
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Your doing the right thing in taking a bike you know. Most people starting out chose a new bike ... that they don't know. Some don't 'like' HD.. their problem.

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The HU is not just about this 'Hubb' board stuff .. do read the other stuff - that will give you the FAQ stuff ... in particular read other peoples ride reports ("GET INSPIRED' at the top), shipping ('ON THE ROAD') etc.

There is/was a russian guy also deaf riding around the world ... he might be able to advise on things he found useful form the deaf perspective?