Can you not set it up and then not have ongoing issues?

That's a tough one to answer, because Linux has one key element that is different from other OS : it isn't one single thing dumbed down to cater to everyone, instead it has multiple variations (distributions), each has their own logic and ideas, and everyone of them are highly customisable (so yeah you can spend a lot of time editing stuff if you want to). This means that it higly depends on what you chose to use, what you wanna do with it, and what are your skills.

I could say that you would get as much issues as you would with any other OS, but that would be wrong depending on the distribution you use, that would be wrong if you have a specific need that isn't easy to get on Linux or not yet troublefree to use, and that would be wrong if you have no idea what you are doing. You could even have less issues (but I wouldn't advertise that thought). This is why there are what people call "noob friendly distros", meaning as much troublefree as possible and easy to learn (doesn't mean it has all your needed features, or that it will grant you the best experience).

I have been toying with Linux since I was 15, but I only made the switch some years ago (I'm 29). Most of my issues were either that the distribution I used did'nt satsfy me, or that my needs were a bit complicated to get working, but once I found something that worked for me most of my experience has been «you configure it once and then you are good to go», I cannot say it is the same for everyone.

One important thing to note is that switching from a familiar OS to an unfamiliar one is never easy (people tend to forget how hard they had to learn using a pc), and it can get painfully hard to do if you go at it with the wrong mindset. So if you want to try it out, I'd suggest you first spend some time looking if everything you need will be available and easy to get working, then find a distribution that you think would suit you (since it's a first dive you might try something "noob friendly"). Ideally you would first look how it works before trying anything, for exemple don't be fooled thinking a distribution is only defined by how it looks, it's how it works that matters most. It's a bit like preparing yourself for a trip, never try it blindly (it's a common mistake people do when switching between OS, be it Linux or otherwise), it will require patience and an open mind because you will have to learn how thing works since it's new to you and it might feel like nothing is working the way it should, so it's better if you can still go back to an OS that is familiar to you if something goes wrong. And then you'll see for yourself if it is a troublefree experience or a masochist one :p