I'm an elementary school teacher who's used Macs for some 30 years. I have a late 2012 MacBook Pro which is showing its age. In looking at Apple's new offerings and trying them at the store they fail in several ways: 1. Cost is way beyond my budget. 2. MagSafe missing is a big deal when you have your computer plugged in with 25+ third graders. 3. The keyboard was just not to my liking and the lack of ports that I need to use without dongles just doesn't make sense. I've looked at MacBook Air, but again, I want a laptop with modern up to date components and I'd like a Retina display. I'm looking for advice and suggestions. I looked at the Microsoft Surface Book and it looked very tempting, but I have no idea how Windows 10 works.
The Surface Book is a great product, as is the Surface Pro 3/4, and Windows 10. I've seen refurb SP3s with an i5/4GB RAM/128 SSD for under $600. That value can only be matched by Apple's MacBook Air (as low as $700), which is, despite its age, an outstanding computer. The SP3 and MacBook Air are the two value products where you get a lot of bang for your buck. Both screens are inferior to newer products, but IMO both are still good screens.
Since you want a retina, price is limited, and since you like MagSafe + the portage, the 2015 13-inch MacBook Pro is probably worth checking out. New models for under $1,000 can be purchased (with an i5/8GB RAM/128SSD), and the 2015 has several options for upgradable internal storage that are not available with the 2016.
The 2016 13-inch has a slightly faster base CPU, faster SSD, the different (and arguably, superior) form factor,
dramatically better graphics, a brighter screen that IMO does
much better in brighter light, better speakers, and a different touchpad/keyboard (you likely know this all already, but just in case...) The version without the touch bar and the 2015 have outstanding battery life, where as the touch bar version has somewhat more mixed results.
The 2016 is a good computer, but personal preferences may align better with the previous generation. The keyboard is something that takes adjustment to, but you may find you like it more than the previous generation after spending a few days with it. The ports, on the other hand, are something that cannot be changed, and (depending how you wish to use the computer) the lack of the SD card slot and USB-A may result in a greater tax on productivity than what USB-C yields (at least for now).
I personally consider the 2016 MacBook Pro and Surface Book to be comparable in terms of overall design: outstanding, not perfect, and capable of leaving most buyers very satisfied. Windows 10 has come a long way and has a bright future - it's not quite as User friendly as OS X, but it's making major strides. Both OS X and Windows 10 can meet a wide range of productive needs, although someone may have a strong preference for one due to OS-exclusive third party software.