Going with the general train of thought on here, I would say the following.
If your kit is serivceable and not on its last legs, I would say keep it and save your money. This applies to tents, sleeping bags etc: you are obviously comfortable with these, when they will perform and when not, so why change?
They may weigh a few more kilos than new stuff, but you can off-set that by packing sensibly and not taking everything. If you have problems on the road, they may not get fixed there and then, but a solution always turns up in a way you least expected....
GPS? Very useful in a new city and can save hours of riding in circles!! However, DO also take paper maps with you for the reasons already given.
Bottom line is if you want to buy new stuff, go for it, but don't feel you have to in order to be a successful overlander on what sounds like a great trip-to-be...
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Adventure: it's an experience, not a style!
(so ride what you like, but ride it somewhere new!)
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