Cash up front always makes one worry, but I can think of plenty of good reasons why someone would prefer American cash dollars to a wire transfer to his bank in Zimbabwe. Hell, I can't think of a single reason why the outfitter would prefer Zim $ in his Zim bank account. Between taxes, inflation, and/or confiscation on a whim, a handful of US$ looks pretty appealing. If I know and trust the guy, I'd probably go for it. In reality, I'm not sure that a wire transfer is any better if I don't trust the guy. If I wire transfer money to Zimbabwe and something goes awry, I doubt I would have much more chance of getting it back than if I had handed him cash. Fact is, there is plenty of trust needed in any of these transactions. I paid some up front on my first trip to Africa and wire transferred the rest once I got home. My outfitter could have screwed me and I could have screwed him. In either case, the money, time, and hassle of recovering the money if something went wrong would probably not be worth it for either of us. Honor and maintaining a good reputation is really what holds the deal together. If we were trying to cover ourselves on both ends, I'd have put all the money up front in an escrow account with a trusted third party that we both agree on, and set up an arbitration process that we both agree on in the event of a problem. If you aren't doing that, it is more or less a handshake deal any way you look at it.