Before you do rooting on your phones, you should consider:
-What you're trying to achieve
-Warranty
-Knowing how to restore factory image to the phone
-Software updates
-How root friendly is your device
-Understand the risk
Sometimes you may not need to root. If you want to remove bloatwares, you can disable apps instead. There are lots of apps that may be able to do what you want without root required. There are many apps to customize the phone without needing root as well, Android is great at that.
If you don't know how to restore factory image, tread carefully. Before you root a device, you should read about how to restore it. A lot of people can run toolkits to root a device, but then get stuck reverting to previous state or restoring the phone when it can't boot.
Also other things to consider is do you need to unlock the bootloader or not to root and/or to restore factory image? And do unlocking the bootloader void your warranty (most of the time it does unless you have a Nexus or Google / Developer Edition). Also some companies may also void your warranty for rooting.
Rooting may cause issues with receiving updates. For some phones, the software update may simply remove the root. For some, the update will not work or will soft brick the phone. You should always assume that things can go wrong when applying over the air updates on a rooted phone and have a way to factory restore it.
If you don't want to deal with things like locked bootloader, system partition lock (S-ON / S-OFF), and all that, consider buying a developer friendly device. Devices like Nexus, Google or Developer edition are easier to unlock the bootloader and root, they generally support "fastboot" so is much easier to restore and therefore more difficult to permanently brick. I would not buy something other than these devices in the first place if I am planning to root at all.
You should know the risk as well. Rooting give you full access to the phone, malware apps may utilize root to do the same, you have to be more careful with what apps you install with root and get them from the right sources.
To answer the original question, how hard it is depend on what device you are using and how much research effort you put into it.