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I'm trying find the cheapest and most feasible way to get from Santa Cruz, Bolivia to Buenos Aires, Argentina. Would it be cheaper to book a ticket once I get to Bolivia? Would a bus trip be feasible?

Thanks!

I had looked into travelling through Bolivia while on-line before reaching S. America. I didn´t find anything I could book through other than airlines, which didn´t help me out too much. Did you find anything (trains, buses)?

If you´re taking buses, I think that once you get to Santa Cruz it should be easy enough to arrange in person. Once you cross into Argentina (probably at Salvador Mazza?) there are a lot of argentina bus companies. I´ve been doing the overnight, servicio cama buses for the 8-10 hour trips. That has run me roughly $70US total for two trips (BA-Córdoba-Salta), but you may be able to get that lower by taking a bus that skips the comfy seats. The bus line maps I see here at the hostel pass through Salta and Córdoba, from Salvador Mazza, before turning towards BA. It also passes through Santiago del Setero which I think has a passenger train line back to BA. Don´t know what a regional airline would cost. Just some ideas..

Bus is the best alternative. Santa Cruz (Viru Viru) has some intl flights but they're too expensive if you are on budget.
For bus travel you have to account at least 36 hrs.
Depending on your itinerary and what you want to see you could choose a route via Salta (Arg), or Asuncion (Par). The latter would be longer, but better if you want to visit Iguazu Falls. To get there you'd need to take another bus trip 6 hrs from Asuncion. Then the bus trip from Iguazu to BA would take 17 hrs.
Night sleeper (cama) busses are recommended on the longer trips.

One more thing...
It's easier to buy bus tickets while you're in Bolivia. Sometimes they are sold only on the actual day of departure. There are usually quite a few bus companies to choose from.
There are no reliable websites where you can puchase your tickets, so the only way is to be there phisically and get them over the counter.

Also...
There are no trains to consider. There are only a few train routes, and only within the country (like in other South Am contriesy

Internal flights within Bolivia are cheap (International is $$$$$$). You can book them when you arrive. Bus is entirely doable when you arrive also and there many spectacular spots to stop off along the road down to Argentina. I went the other direction i.e. Buenos to Bolivia but you can get an idea of highlights here. There is a train from Salta to Buenos Aires (takes around 24 hours) but you need to book that well in advance. Have a great trip!