I've never understood why iTunes is the way that it is, except that was already available on Windows, so it seemed like a good vector for devices. It really is a jumbled bag now though, and seems to go through significant UI changes every release for no good reason (hearts? stars? iTunes has them both!)
OS X used to have a separate syncing application, iSync, for PDAs that was simple and generally worked. I was dusappointed when the moved everything into iTunes (really, calendar and photo setting in my music player?)
What is the concern with USB and power? I really like lightning and MagSafe.
Uh, there is strain relief. On every cable. You're probably doing what everyone does, which is to wind that cable on the power supply as tightly as you can around the charger, which is going to eventually break the cable. Instead, make a small loop where the cable begins, then wrap gently. It will last essentially forever.
And no. This isn't a "well known design defect". In fact, Apple's cables are inevitably designed and manufactured better than competitors'. Have you even seen the awful mess that passes for PC power supplies lately? At all? Well, I have, since I administer about 200 Macs and around 75 PCs. I can tell you that there is no comparison in design or quality.
I have a MBP from 2008 with the original t-shaped magsafe power cord, and its still in perfect working order. Maybe you're harder on you're harder on your power cables than you're giving yourself credit for.
Daycare should really receive government subsidy - the extra income tax they earn can be used to cover the gap.
In The Netherlands we have a 33/33/33 model - parents pay 33% of the costs, the state pays 33% and the parent's employers pay 33% (which is an extra charge split over all workers).
In recent years they've tweaked the model: parents with 2 x modal income pay 100% of the costs (and their employers also pay 33%). Only the lowest incomes hit 33/33/33.
For the 2nd+ children the subsidy is much higher for all income groups.
We send our son to daycare for 2 days a week, costing ~700 EUR/month. My wife works 36hrs (4x9) and I work 40hrs (4x9,1x4 at home). Grandma/pa do one day (the other grandparents live in the UK). I really like this mix - he gets 4/days week of parents, 2/days a week playing with other kids and 1 day of being spoilt by grandparents.