In spring 2011 me and four or five friends are flying to Ecuador to stay for a month to rent a house and surf. After that month is over they're flying home with exception of my friend Adam.
Me and Adam then want to buy motorcycles/dirt bikes and travel through S.A. on the bikes. Were both 21 years old and plan on doing this differently than most people with the newer nice bikes and multiple luggage cases mounted on the bikes.
We've both rode bikes for our whole lives, motoX and crotch rockets so our riding ability is quite high. Luggage wise we will only need like two bags, a backpack and a bag, bungee corded to the bike. Were great at packing incredibly light, we want to stay very mobile.
I have some direct questions listed below, but really any tips/links are appreciated!! I will also cruise through the forum for info. Thanks, Paul.

What can I expect to pay for a reliable bike?
Does it have to be street legal or is a dirt bike OK?
How hard is it to buy a bike in SA? I'm an American citizen.
Can I sell it after my trip ends?
Cities/spots you think are very fun or must see?
How should I carry my cash? (keep from being stolen)

Steve

Will try to answer a couple.

What can I expect to pay for a reliable bike?
Due to high import fees you will pay more than in US, Would be cheaper to buy in US and have shipped to your location. Non resident buying vehicles can be a major problem and may cause problems at border crossings.
Does it have to be street legal or is a dirt bike OK?
It will need to be street legal.
How hard is it to buy a bike in SA? I'm an American citizen.
Can be major problem, see other posts
Can I sell it after my trip ends?
Not legal generally unless you sell to someone from country where it is registered and they transfer title there.
Cities/spots you think are very fun or must see?
Unless you have a couple of years you will never see it all but check the travel stories for ideas on what to see.
How should I carry my cash? (keep from being stolen)
Use credit cards and cash machines (found most everywhere), debit cards better because of limit to what could be stolen. What cash you take should be in mulitiple places, some hid on bike, money belt, in boot, etc. Always carry two wallets, one a "muggers wallet" with only a small amount in it and some old credit cards.

You need to spend some time going through posts here to get an idea of what to expect and how to make it work.

Bob

Having recently purchased my 4th motorcycle in SA, I decided to put together a buying guide together on my website, it's not finished but it might help you somewhat. You can find it here.