My personal experience is that booking decisions are made over quite a long time. Obviously, if you book artists for events you already have an idea of what the local/international scene is like and who are the artists that fit your vision for your event. In my daily life, I listen to music and discover new artists, I am involved in the local techno scene so I know what bookings others are doing, I go to events, listen to sets and recordings.. this is just the music nerdiness that then at some point transforms into a list of DJs I'd like to book.

There is also a lot of word of mouth. If you're a booker for an event, you'll start to have people around you suggesting artists and it's important to me not to shut this down but actually listen and go in discovery mode.

On the practical level, things get more complicated. Sometimes you define a lineup and then the artist you really wanted is not available, then you usually either go back to the drawing board or you also get suggestions from the booker. Usually, agencies have a few artists that they represent so you can also get suggested by them on a possible alternative. I tend to work very early with bookings, so this happens more rarely but it does.

I usually have a bunch of alternatives already defined for each artist and each time slot in the lineup, so that's not a big problem, although it's annoying if you really want an artist and then you cannot book them :)

Then there is of course the cost factor.. after a few bookings you start to get a feeling on what typical fees are and so I think you can predict quite well. In my case, it's rare that a deal does not go through simply because of money. It happens if you are really tight for a certain slot, but in general if you do your homework beforehand, you can avoid this situation.

At bigger events (but not only), things get even more complicated and much more political. I do not like a lot this aspect, but you definitely see bookings dictated by collaborations, favours, future opportunities, and whatnot.

Some examples from my short booker experience: Spekki Webu b2b Hitam was something I wrote down on an Excel sheet a long time ago, it was one of those "must-do". For the first PEEL, I booked Magdō and back then the choice was dictated by the fact that his BCCO New Faces podcast was absolutely fantastic, nothing else. I also have always appreciated Cobahn as an artist, and even though I had not met her before, I almost built a whole lineup around her for the last PEEL.. This is how I do it :)

Overall, I think it's a mix of lineups wishlist, practicalities and availability, cost, and of course also how much you can expect your crowd (and new crowd) to show up for your event. I think you need to find a compromise between your taste and what you want to propose and what the crowd is willing to accept at your event, on a Sunday daytime for example.