I'm in the market to buy a new laptop to replace my old in years but young at heart Dell Latitude. (I've had the Dell in 2012 when it was at least two years old then.)

I'm a Windows guy, and have been for some time, but I've always wanted an Apple.

I found a couple of Windows laptops that I'm digging.

The first one is a Samsung Ativ Book Pro 9.

http://www.cnet.com/products/samsung-ativ-book-9-plus/

It's a light ultrabook with a 13.3" screen which runs at 3200x1800 an Intel Core M chip and 8GB RAM. It also comes with a SSD - either a 128 or 256 GB drive.

The other Windows laptop is the Dell XPS 13.

http://www.cnet.com/products/samsung-ativ-book-9-plus/

It has essentially the same specifications as the Ativ, although I like the look of the XPS.

Then there's the Apple MacBook Air and MacBook Pro.

http://www.apple.com/macbook-air/

http://www.apple.com/macbook-pro/

I have a Windows Phone and an old Surface RT tablet, so I'm invested deeply into Windows, but unless the Surface Phone is available on T-Mobile, and judging from T-Mobile's decision to pull Lumia's from its store it won't be, it's not likely I'll keep my Lumia. So I could go ahead and make the switch to an iPhone and MacBook of some model.
But I'm wanting to develop some web development / software development skills and there are simply many more options for programming tools using a Windows machine.

I take my laptop out of the house alot, so the physical size is important to me. It's a close #2 behind performance.

Some days the laptop would be used in a home office setup which may eliminate the Air because of the limited number of ports for a monitor or peripherals.

Most of the usage would be for digital development (web design & development, some app development), web surfing, the odd game here and there.

If you have an Apple and you switched from Windows recently, was the switch a big deal? Would you recommend to any Windows user to swap platforms?

If you've used any of the Windows notebooks, do you recommend either of them? I know the 'Retina' display is overkill, but I do plan on connecting the laptop to a monitor, which would give it a use.