My personal preference is overclocking. A cpu that's 'enough' tends to struggle sooner or later and by the time that happens a generation or so of cpu's and their motherboard sockets have passed meaning a new replacement is rather costly. With my 4690k overclocked I can easily get i5 6600 performance from it. It meant a z series board and a better cooler which were a bit more. I planned already to use an aftermarket cooler, for looks and for performance. Not everyone cares what it looks like or cares about noise. By going with a big air cooler even oc'd my i5 is whisper quiet and I like that.
On the other hand, If I had to upgrade to skylake it would mean more than $30-50 for a decent cooler and $20-30 for a nicer motherboard. It would mean a $200 cpu and another $130-150 motherboard. Ouch. The fewer times I have to do that, the better. Not counting having to buy ddr4 ram, having to reinstall windows etc. Not to mention the performance that people were waiting for to release with skylake I was enjoying for a good 12-18mo before it even hit store shelves. So to me personally it's worth it.
There's also the price/value factor. You mentioned z170-ar and the 6600k. A $160 motherboard isn't a 'requirement' to overclock. There are cheap z170 boards for $90-100 and solid oc choices in the form of $120 z170 boards. So is it a $150 investment over the top of a non k? Depends what parts you choose really. I can make it a $500 difference if I go with something redonkulous like a $500 z board like the gigabyte gaming g1. It also depends on which cooler, a $35 cryorig h7 or $100 h100i? In other words it 'can' be a lot more expensive to overclock but it doesn't 'have' to be based on parts chosen.
The 6600k itself is only around $20 more than an i5 6500. Granted with the k series you 'have' to buy a cooler since it doesn't come with one. A 6500 does come with a stock cooler so you could save $30 or so there. Me personally, that stock chunk of metal never even makes it out of the box, it's not worth my time. It's a personal choice, not worth the headache of fiddling with the stock tim, the cheap plastic pushpins plagued with problems, the potential for loud noise when the fan ramps up under load. Generally I keep my builds and they meet my needs for 4, 5, close to 6yrs at a stretch and the cooler stays on the machine all that time. Over 4yrs, $30 is something I can live with.
Some people upgrade every year or two and if that's their situation then cheaper parts may be the way to go. The way I see it, even if it were $100 extra if it's a device like a pc that I use daily it's worth it given the time I'll use it. If it sat in the corner collecting dust all week until I decided to check my email then no probably not.
To put it in perspective, I spent a weekend with some friends. We went and had a simple lunch, I helped pay for groceries for a cookout, we went bowling. Nothing fancy and it was over $100. A couple of nights skipped going out to eat over the course of a year will easily make up the cost difference. Then again I'm a pc enthusiast so it probably rates higher on my priorities than it may for someone else who just wants a machine to do a task.
In terms of time spent tinkering, it didn't take long at all. I made a few changes in the bios, tested with p95, asus rog realbench, intel burn test and xtreme tuning utility and it took all of maybe an hour or two. It's not something that requires time out of my day even once a week. If only gaming on it, then no overclocking isn't going to net you 10-20fps improvement on every game. If doing other tasks then yes it can be a benefit. It's not necessary but I consider it a perk. Just different ways of looking at it and overclocking isn't for everyone, it's just an option.