GoRoadTrippin Hey Sophia! I've been dreaming of a trip like this, I would love to climb up Mount Kilimanjaro. I actually can also help with booking and finding a local guide to help us out. I'm a travel writer and I've been doing some work with Safari Africa Adventures - I work with Eliya Tumaini, an AMAZING local guide (you can check him and his last company, Nature Bound Africa on TripAdvisor). They have great treks up Kiliminjaro (http://www.safariafricaadventures.com/product-category/tanzania/kilimanjaro/), and since I've been collaborating with them, I'm sure I could get something like a 5% discount as well.
Anyway, let me know if you're still planning a trip, my schedule is pretty flexible, though the summer months are better for me generally.