Hi Tom, welcome, and good luck with this question, and especially with your Great Safari To Come! You'll get lots of feedback here, I'm sure.
At the risk of complicating your life some more--have you checked the commentary on Tents in crazyguyonabike.com? Or maybe that was part of your research? I mention this because you'll find numerous prolonged, informed, detailed, opinionated commentaries there -- you'll notice that I have so far refrained from saying "Tense discussions" and all the other bad-'cos-obvious related puns...
But an opinion on a tent, because my tent is one of the one you list:
1) MSR Hubba Hubba: Have had one for four years now, and have used it for hiking, paddling, cycle-touring and motorcycle touring. All in all, I've found it to be a good balance of cost/weight/space/quality/ease of pitching & striking, with some qualifiers:
> other people have had problems with the tent (see various CGOAB threads). It may even be that the Hubba Hubba is no longer sold, because it violates flammability codes.
> I've encountered condensation problems, which might / might be resolved (or at least counteracted) via a vented fly, such as the one MSR now offer on their "Nook" tent.
> you can't erect it in the rain without serious risk of getting the inner tent wet -- I compensate for that by using an ultralightweight tarp (Integral Designs Siltarp) & would recommend one of those no matter what tent you buy.
2) I have used my Hubba Hubba in all sorts of different locales & conditions, but for relatively short trips (i.e., up to a month). If I were to do a Grand Safari like the one you're considering, I'd look at a Hilleberg or a TarpTent rather than the Hubba Hubba.
My reasons: The former seems to offer better all-around quality and hence durability, and both can be pitched in the rain while keeping the inner tent dry. One consideration is whether to get a 4-season tent or not -- i.e., one suited to winter camping. That would depend on how you approach seasons and altitude. You'll be carrying extra weight with a four-season expedition tent -- perhaps for that reason, the TarpTent is worth a close look.
You would also expect to spend more than I did on the Hubba Hubba. But, beware the Dreaded False Economy here -- you do not want something to go seriously wrong because a fabric/zipper/pole/etc fails in a dodgy situation. At altitude, or in the winter, negligence or bad equipment or "it seemed like a good idea at the time" can mean disaster, and in short order. Sorry to sound apocalyptic, but...
3) Summary opinion/recommendation? Um, er, "It depends" -- on factors such as those I've outlined above.
Hope this is helpful nonetheless.
J.
