You're talking about doing exactly what I plan to do. Plenty of common ground there. Do you think you can get up Kilimanjaro significantly cheaper if you have boots on the ground in Tanzania? Booking stateside through the Internet is $2500. Which is decidedly nonmustachian. I have heard legends of the women in EE and SEA and am basically holding off on long term relationships with American women until I have a look
Point 1: yes, absolutely you can do everything cheaper in Africa once you have boots on the ground. This is pretty much always the case in the developing world. If you go too Western you're going to pay more for things than you'd even pay at home. Since you're young and single you can take more calculated risks with local deals. I no longer have this option because I'm married and my occupation forces me to strongly consider security. Thus, I have to pay more to have a more guaranteed situation.
Point 2: you're a smarter man that I was. I wish I would've done a gap year to travel EE and SE when I was super young, in super good shape, and single. Just take the necessary health precautions.
Side Note: this is slightly related to #2, but is more overall advice. People will think you're rich just because you're American (or outside of Europe, if you're white). Avoid overt displays of wealth and just accept this fact. If you're just looking to have fun with women, that will work out great for you. If you're looking for love, be aware of the fact that many people are chasing money and/or visas.
I recommend not booking Kili until in Nairobi or even in the town near the park entrance (can't remember the name). Friend and I went there 1997 with no reservations except flight, caught a minivan to that town, paid $300ish total (three hundred) for 6 day trip on the "coca-cola" route. We we grouped with 2 others that had paid $2500+ each for the same terrible food, guide in flip flops, etc. There are no guarantees to be had from your computer in the states. Your actual guide does not get the memo about what you were promised for food, etc. Everyone uses the same huts.
Book those flights today, dammit!
