I have already successfully summeted Kilimanjaro (Umbwe Route), and as I stated previously, I understand the appropriate climbing dates, which is why I chose to attempt it in July.
That said, I suggested a shorter route, due to the fact that I currently live in South Africa, and unlike American schools, our vacation periods are quite different, and our July vacation is quite short (under three weeks), therefor it would be best suited for a shorter hike, yet I fully understand the aspects of acclimatisation.
Thank you for your suggestion on climbing Aconcagua, I will certainly consider it.
Tanner: Unfortunately we do not have summer break... Our vacations are spread out throughout the year, and our school year is spread from January -December. (With a long vacation from the 4th of December, to the 21st of January)