@FallowJaeger, you pose interesting questions. Before answering, it would be helpful to attend to some definitional issues.
First, you use the term "quality animal". Secondly, you say "best animal".
While many of us might agree on what the terms mean, I know that many others of us would not. For me, a "quality animal" is any animal which has not been handled in the manner of livestock, and which can be hunted in a fair chase manner, even allowing for fences (properties large enough for the animal to live out the normal life and behaviour of such animals in the wild).
Equally, for me, the " best animal" is almost never the one with the biggest horns, or the largest mass, or whatever. I look for old animals which, while they might not have the best horns, have gotten old by being smart. Alone is better, and past breeding is best.
This is not to say that those who look to achieve a record, SCI or Rowland Ward, are not right. When I went elephant hunting, my goal was 50 pounds a side or better (which shows you the variety of responses you can get to your question). We all have goals, and mine include the nine spiral horned and the tiny ten, for example. If your goals include a 60" kudu, then by all means go for it.
I would say this though, by way of general advice. Look for a big property. Big is of course relative, but it has to be big enough for animals to live and die "naturally." There are so many BIG properties in South Africa and Namibia that you don't need to settle for a small property. And tell your PH that you want to hunt, not shoot, and that you want to get as close as possible to the animal. You will bust more stalks that way, but if you aren't focused on how many animals you can shoot in a day (as I was on my first safari to South Africa), the experience will be worth it.
I also recommend you not shoot from a vehicle, because that's not really hunting. I have done that and while it is legal in most of Southern Africa (depends a bit on the country and type of property), to me it's shooting (which is fine if that's what you want), but it's not hunting.
Good luck with the first hunt!