It’s always hard to know the best time to buy things. But for electronics the main question is how rapidly the technology is evolving. 
For things that are moving fast it makes the most sense to try to buy “ahead” because the software typically will end up depending on new features. For instance phones are roughly 10x faster now after 2 years. So most software is unbearable slow on say an iPhone 4s vs and iPhone 6.
On the other hand, some technologies have really slowed down and with rapid price declines things that a generation or two older are terrific buys. For instance Intel absolute processor performance is perhaps only 20% faster after two years. So an older Broadwell systems is about as fast as the new Skylake. The big change is having the right SSD as the latest ones are 4x faster. 
So here are my recommendations by product category for going fast or slow and then where you should look:

iPhone: Buy now, on a September cycle

These are on very rapid improvement right now as the processors are so much faster. The iPhone 6s and the iPad Pro are basically Intel notebook class systems. So if you can afford it, I’d say get as close to the leading edge as you can. These things also hold their value really well if you don’t destroy them. Typically after two years, they hold half their value.
One interesting option are the new Apple Upgrade Program which include AppleCare+ and gives you the right to just trade in for a new phone every year. Here is how to figure out how to buy them.

MacBook: Wait for Skylake

The same is true for MacBooks. There are two trends right now that are not processor related. The first is the move to very fast SSDs. The so called 4x PCIExpress NVMe devices improve real performance remarkably. It is 4x SATA. And the new Skylake is out so probably a good idea to wait

  • They have a great redlight/greenlight view of what products to buy and what the product cycle is
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I’m Rich & Co.

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