Everyone will have their own point where they say enough is enough. I see two concerns, cost and the headaches. Cost is something I balanced and accepted, I wanted to hunt in Africa with my own rifles and was willing to pay a certain amount to do it. Everyone must reach their own cost acceptance level.
I can't speak to bringing my trophies into Canada just yet, that is about to start, but I can speak to two factors that made our hunt so much less stressful: the issues of hunting with our own guns and flights in general. The price of hunting in Africa from North America is going to be what it is, can't do much there, but I do highly recommend the following to make for less headache and hassle:
1. Get a travel agent. Many will say you don't have to and that may be true for them; it was my initial thought also. Well, let me tell you,
@Just a dude in BC and I are glad we did. Even though we live in Canada, we went with
@TRAVEL EXPRESS. The cost was not that much more and the service they provided was so worth it. Not just booking three flights each way with the same airline group thereby luggage checked all the way through and if any delays it's easier to deal with. They got us emergency exit seats with extra legroom in the econo class when they could, confirmed our travel with firearms 72 hrs prior to boarding with all airlines, advised on the required paperwork, contacted ATF to confirm we did not need to have importation paperwork to transition through Atlanta, when WestJet changed their flight times for our return from Atlanta to Calgary causing us to not have enough time to catch our connector to Victoria, they sent emails while we were hunting giving recommendations and sorting out alternative flights. We didn't have to do any of it and had a much more enjoyable hunt as a result.
2. Get a pro to sort out the firearms paperwork (SAPS for South Africa for example). We went with Afton Lodge, paid our very acceptable fee and had zero problems. They took care of it. So worth it to bring our own rifles to hunt with and not have any issues.
You will have to decide when enough is enough, but just a couple tips we found to make the hunt easier.