Lots of talk about disc brakes. I don't have experience of that, but do of rim brakes.
Traditional rim brakes come in various guises. Cantilever brakes were all the rage when I built my first mountain bike almost 30 years ago. If set up right, they had impressive stopping power against the other brakes of the day. They were not the easiest to get set up, but worked well once correctly adjusted. But every brake change brought with it the same challenges of getting it just right.
That same bike got upgraded to V-Brakes 10 years ago. That bike had been demoted in favor of another bike that was purchased with V-Brakes which I had already found to be easier to maintain and, with slightly larger pads, a little longer lasting. A friend upgrading his group set donated me new levers and the V-Brakes for my stash of spares. One bored Sunday I upgraded the old MTB to V-Brakes and immediately gained the benefits of easier pad changes-servicing over the old cantilevers.
Fast forward to my Rohloff bike with HS33/HS11 Magura hydraulic rim brakes. Slightly better braking power vice good V-Brakes, a breeze to change the pads and brake strength adjustment a doddle with a simple allen key on each lever to adjust.
Brake failures?
The most common failure in my experience is a snapped cable on the cantilever and V-Brakes. Cheap and easy enough to fix. A cable can last years or just a few months. Getting teflon cables can help hinder wear hidden within the cable outers. A frayed cable might give you advance warning to replace, but I have had cables snap on the end stopper with little to no warning. Water ingress can cause corrosion, and sticky returns of levers when released might be a reason to check, grease or replace a cable inner.
I've never had brake rubbers break off on any system. But trying to stretch the life of a pad can be a false economy. As you adjust the brakes to use all the remaining surface you eventually expose compounds or metal within that will EAT your rims. Brake pads are cheap and can be replaced in a jiffy. Rims are not.
In the same way, riding on rim brakes during the winter can leave debris lodged in the profile of the brake pads. This will worsen your braking power and wear your rims. If you hear a scraping noise under braking, and the pads look like they have not yet reached the wear marks, then an inspection of the pads might find foreign bodies lodged in the brake rubbers. These bodies can often be quickly removed with a small knife or screwdriver and all should be good again.
On V-Brakes and Cantilever, although the brakes themselves are relatively cheap, I invariably found pads would eventually wear unevenly, especially if just tightened using adjusters on the levers without recalibrating against the rim itself- hastening service intervals. The Magura brake pads might cost a bit more, but do brake more evenly across the whole surface area- thus extending usable pad life.
Magura brakes are a closed hydraulic system. No cables to snap. Not infallible, but more reliable than cheaper cabled brakes. My Rohloff bike must be around 15 years old and still running on the same brake system. I've owned the bike around 2 years and have ridden 13,500km on it. The only brake incident was self inflicted as I adjusted the wrong screw and lost the hydraulic oil in my rear brake. Luckily I was able to fix this on a long bank holiday weekend using my Rohloff oil change syringe (same size as Magura fill hole) and some baby oil instead of Magura Royal Blood. But had I not been at home with the necessary tools and internet to help me with tips I would have been stuck without any braking power on the rear.
If you go for rim brakes, I would personally recommend Magura. But also read the manual, or watch the you tube videos BEFORE attempting adjustments the first time to avoid the sort of pickle I put myself in just described. Other than that one incident, I just find the Magura system superior in reliability and in maintenance than traditional rim brakes. But V-Brakes are also perfectly usable and safe if maintained. But consider that routine adjustments and pad replacements are a little more time consuming than Magura. However, if you were planning a longer tour, cabled brake parts and pads can be found the world over. Even larger supermarkets sometime stock these. Magura or disc brake parts are not always available in every small town bike shop off the shelf, and might force you to stop a day or so for parts to be delivered. But same deal riding a Rohloff too.
Regardless of brake system you go for- visually check your brakes regularly for signs of wear. Prevention is always better than cure. Cables are cheap, so replace on signs of wear or corrosion. Pads are cheap too. Do the same with them. If you notice the brakes are less biting than you are used to, learn how to adjust so that you always have the optimum braking power for your riding style.
At the end of the day, brake maintenance is more important that any other maintenance on your bike. A skipping chain, a creaky bottom bracket or rattling mudguard are unlikely to land you in A&E if they fail on a ride. If your brakes fail, it could be game over for you in a second. So check regularly visually- and whenever you are out on a ride. If something is not right and cannot be fixed on the roadside, then consider all your options. Walking home is always a better option than one involving blue lights.