I am new to this and looking for some pointers for places to start my trip research. This forum looks like it has lots of knowledgeable people on it so hopefully someone can help me!
In September I jet off (from the UK) to Costa Rica for a Raleigh International expedition which finishes mid-December. After this I would like to find a relatively cheap route down to Santiago, preferably overland. From the map it looks like going through Panama (I've got a bus time/price from Ticabus.com for this leg) and then through to Bogota, Lima and then Santiago. Does anyone know where I can get information on busses/trains/planes for these three legs of the journey? Has anyone done anything similar? Is it dangerous? I expect to be travelling alone unless I meet someone on the Raleigh expedition who wants to join me. (Single white female... is that dangerous?)
I haven't even begun to think about places to stay or money that I will need. Somewhere I may need to get some casual work to help keep me on the road - does anyone know how likely/possible this is?
I know that's a lot of questions and that they're very vague so far, I'm just starting out so if any of this sounds ludicrous please also let me know.
This is indeed a good place to do some research. Check out the existing threads, you'd be surprised at the questions already asked.
Panama -> Santiago, there is no overland route across the Darien Gap, a swampy section between Panama and Colombia. You will need to fly or take a boat to Venezuela, Colombia or points south.
My experience of traveling throughout Ecuador, Peru, Bolivia and Chile is that you don't need to worry about bus companies and timetables until you are ready to go to the bus station and get on a bus. There is an incredible diversity and selection of bus companies that will get you anywhere at just about any time of the day and night. You're talking about some long distances, overnight buses are relatively safe (keepy your wits about you and your daypack wrapped around your legs) and you can cut the cost of hostals and wasted daylight time.
I can't speak to the possibilities of casual work from direct experience, but I wouldn't count on it. Places like Peru and Bolivia have high unemployement rates, and those that work don't get paid much. There is always the possibility of working at a hostal for a few weeks, you might try that. And teaching English is a good possibility, though I have no idea what the work visa situation might be.
You can always find a job teaching English without a work permit in B.A. Argentina and some other places in S.A., not Ecuador, Peru or Bolivia, etc. but the hours are long and staggered (you may have to travel 2 hours RT on bus and subway to teach one class)and the pay is low, sometimes if you have a special skill or are very good with people and outgoing a small tourist hotel or hostel owner may hire you, again at low pay, being a non resident.