So basically the biggest argument that I can see you making is that with Apple it's easy - you just pay the extra cash and are sure that the hardware you're getting will work without you having to care about making a choice.
I think I can agree with that. Outside of Apple every company offers major choice and products ranging all the way from cheap and shitty to high-end, and in every price range you have to know what you're buying.
In my opinion it doesn't make Apple the best choice. It makes it the Pizza Hut of "Italian" restaurants. It's good enough and quite good in quality, but there are better choices if you know what you're doing or care to ask.
Well, if someone asked me for a reliable 1000$ laptop I'd just tell them to get the T-series Thinkpad. If someone asked me for the best 1500$ laptop I'd tell them to add more ram or bigger SSD, or just buy the initial version and save 500$. Sounds pretty easy.
There's usually no rule of thumb for buying electronics though. I'd say in the 500-700 range you have to pick one that's going to be the best for you as well.
I think I'd know good enough not to buy a shitty product. Guys selling electronics at electronics stores are no experts, I bet I'd know more after a couple hours of research, coming from a relative newbie. I wouldn't need to know details about material chemistry. All it takes is to gather a lot of opinions and reviews, and compare which product seems to serve my needs the most while at the same time gaining 10 out of 10 reviews. I think I'd learn a lot in the process as well, so that sounds like a perfect thing to do.
Microsoft's OS updates aren't as frequent and a 2010 OS is still very fresh, also a Windows 8 Pro upgrade if you're coming from Windows 7 or XP is 40$.
iWork is not MS Office though, and MS Office for Mac is also expensive. If it comes to great alternatives you can download Open Office and it's free.
I wouldn't, I'm pretty sure the T-series Thinkpads are more reliable, not only cheaper. At that point picking either of these I'd know I'm getting the highest quality tech anyway, and T Thinkpads are technically superior laptops. I'd say with these Thinkpads you get what you pay for, while with Apple more cash ends up in their pockets - that's an annoying thought.
That's only an example though, because T-series Thinkpads is a specific, trusted line of products. These days I think the whole "company vs company" thing is a little outdated. It's usually about product vs. product these days. Apple is specific because it still serves the old-fashioned "I want a computer from company X" people. I don't think any person in the tech world who isn't ignorant could just say something like "buy Samsung/Sony/whatever" because each of these companies have amazing products as well as shitty products. You see these silly trolls on the message boards saying "Samsung sucks, Sony rules, only Sony!" - that's how you tell that someone is an idiot. There are maybe a few LINES of products that are worth recommending, like the Galaxy S series (although there are shitty phones there as well, like the Galaxy S Advanced or PLUS versions of phones). Xperia line? Mostly shitty phones with just a few very decent models.
LG releases shitty phones with maybe 2-3 good models a year. Saying "buy LG/Sony/Samsung" would be a suicide and a very stupid thing to do.
However each of these companies have at least 1 product that is better and cheaper than Apple's best Iphone, you just have to know which one it is. Same story with laptops.
Buying a product it's important to forget all the silly prejudice and go for a product that at that specific point in time seems to serve your needs best. It's different with Apple though, because they only have a few products, which severely limits your choices, you know that you're going to pay too much for what you're getting, but you know it's not going to be a bad product. It's paying too much for just not having to care or educate yourself and not having to worry because Apple can afford not having shitty (low-end) products. They basically have these one-size-fits-all products for people who are afraid of custom tailored ones. It's a safe but lazy choice and you're paying more for making it.
You don't have to use it, it's just something Thinkpads often include, being also business computers. Here in Europe it might sound like a much better idea as many countries offer free wireless 3G internet Sim cards thanks to EU's informatization program. Technically you have the internet 24/7 without having to care about looking for open wifi.
You don't have to really like them, I said Lenovo computers might not look as good but both carbon fiber and titanum that Lenovo use for their covers are much more reliable and more expensive materials. It's just how they roll.
The physical buttons there are not for the touchpad/trackpad, they are for the trackpoint, the red pointing stick thing-y. To me it's the perfect replacement for a mouse on laptops and makes touchpads redundant and clumsy. I literally played counterstrike on that and owned noobs. You can use it all day as well, because all you have to do to move the cursor around the screen is tilt the finger, and it's very precise. For people who are used to it, they'll usually say it rocks and is better than a mouse in most scenarios.
Just look at this:
I think you're good, the 2,4ghz core 2 duo isn't really that much slower than the i3 or i5. The SSD drive makes a bigger difference.
I like what Apple did with the Retina display. Displays on laptops have always sucked compared to good PC displays and phones. Lenovo used to sell some laptops with IPS panels but they apparently stopped because of lack of demand oO