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luggage for a weird itinerary

I'm going to Kenya for the first time (first time in Africa, period) in late Feb/early March. I'm prepared to purchase new luggage, sinceall I have currently is a small carry-on roller bag appropriate for domestic travel.

My problem is that none of the "what type of luggage do I bring" advice I'm finding online seems to fit my situation. Here are the pertinents on my packing needs:
1. I am a relatively petite female
2. my flights there and back allow 2 checked bags free. I have domestic connections so I will likely be hauling all my bags through the airport between domestic and international on both ends of the trip
2. after I land in Nairobi, I'm leaving the next morning on a 4 day/3 night safari that will terminate in Mombasa. accommodations seem to be a mixture of camps and lodges, and this safari company said they "can accommodate large luggage"
3. in Mombasa, I will be staying in an all-inclusive resort for my friend's wedding - since she is Indian and the wedding is a multiday event, this means at least 3 dressy outfits and all the female accouterments required for that kind of event - and that stuffing the clothing for this portion of the trip into a duffle is not adviseable. I'm normally a t-shirt, jeans and no makeup girl but in this case, girly packing is not optional. aside from the dressy occasions. I'll be in Mombasa for 6 days/5 nights.
4. after the wedding, another 4 day/3 night safari trip, this one starting with a flight from Mombasa to Nairobi and proceeding by van from there (to Massai Mara). I'm given to understand that these domestic flights usually have size/weight limitations but I don't know how restrictive those will be in this case. note, this is not an air safari, we're just flying between cities then departing from Nairobi (I assume that will be a bigger plane than what you'd get on an air safari?)
5. departing from Nairobi for home. 24 hour layover in Dubai.

Sorry if that's a lot of detail - I'm very excited about this trip, but I want to plan for comfort on both the safari conditions and the wedding/resort without:
a) having major problems schlepping in safari or airport conditions
b) being awkwardly ill-prepared for either environment
c) having some or all of my luggage lost, stolen or unable to fit the transpo requirements (for this reason, I've been told that shipping my wedding luggage is a terrible idea)

experienced travelers - any bright ideas on types of luggage, and/or tricks in dealing with the wedding luggage while on both safaris?

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