One of the hardest things I've ever had to do was to help name my children. I only have two kids, so I'm not sure what happens if we have more. I don't know if it gets easier because we'll be too lazy to care ("Your oldest brother was given your grandfather's middle name and the first name of my best friend growing up. We're kinda sick of explaining all that, so we named you Tim because it's easy to remember and impossible to misspell."). Or it may be more difficult because of name shortage. I mean, it's not like we would skip a possible name to save it for a future kid. ("Ooh, that's a good one. Let's save it for our fourth child. We'll just use this first one for practice.")
All I know is that the naming process was difficult as it was. You want to pick a name that is unique, but not weird. And it has to be normal, but not boring. And it has to flow with a good middle name and you have to make sure the initials don't spell D.U.D. or something like that. And then you have all your family and friends giving unwanted advice and various opinions. And you start remembering every person you've ever met with that name. And then you have to think about what that name will sound like when they’re a teenager or a parent or an uncle or a grandparent. And then your brain explodes, and you pick the first one that popped into your head when you first discussed it 3 years ago. Fortunately for us, that worked out great. My wife and I came up with two solid names for our kids. We were willing to give up the unique requirement on my son, and we gave up the easy-to-spell requirement on my daughter. So we came out okay for our two. But I've seen some other people who just failed miserably.
I actually saw a baby announcement in a newspaper for a boy named DeHansome Troychristopher. I don't remember the last name (and I wouldn't include it here anyway), but I thought it was pretty sad. That boy is gonna have some major issues growing up. Forget the fact that part of his first name is misspelled. You have two middle names merged together there. It's like they were trying to put a bunch of great band members into one to form one of those super groups. It would almost be better as "Troystopher." Well, maybe not now that I see it in print, but still. If it's a tie between two names, flip a coin. Merging stuff like that never works out. What's next, morphing Joe and Nathan into... Jonathan? Oh... wait.... Okay, bad example. You get the point though.