You are hiring somebody with their own catalogue, and around here that is not a formality. Plenty of the writers working the northern rivers have songs of their own they play every week, and the share of the night those take up is worth agreeing in advance instead of discovering in the second set.
Put the ratio you want into your opening message. Mostly familiar songs with a few of theirs threaded through is the usual function shape, plenty will take an all covers night without blinking, and the ones who decline are telling you something useful about themselves rather than being difficult.
Top picks are the acts in this category in Byron Bay, without a review, rating or premium ranking: all these sort keys are tied.
Almost all of them do both, since that is what keeps a musician working in a town this size. Agree the ratio beforehand and name a couple of specific songs you want, giving at least a month for anything new. If a writer says plainly that an all covers night is not something they take on, read it as them heading off a bad fit.
Smaller than the town's reputation suggests, and short enough to read in one go. Work through it sideways rather than downwards, writing to all of them in one sitting. If nothing is free, ask who will travel down from the Gold Coast or across from Lismore and Ballina, since that is a normal night's work for a solo player with one car load of gear.
Less than people expect, which is the advantage of this booking. One voice and a guitar through a compact speaker covers a ceremony and a hundred guests in a soft space comfortably. An open lawn with wind is the hard case, because a small rig has nowhere to hide, so describe the site honestly and let the performer tell you whether it needs a bigger system or a different spot.
Listen to the writer's own songs first, even if you plan a set entirely of covers, because their material shows you their voice and temperament faster than a cover version ever will. Then look for live footage from an actual booking rather than a studio take. Finally, read the reply: the ones who ask about the space, the guest numbers and what the music is competing with are the ones who have played a hundred of these.
Hinterland properties out past Bangalow and Federal, or a rented house with a long gravel driveway, are where the work actually happens. Give the real address and tell them whether there is power at the spot, because a paddock and a bar courtyard are different days.
A ceremony on grass or sand with no outlet nearby only works if the performer owns a battery powered speaker, and not all of them do. Ask how long it holds and whether they carry a spare for a later set.
If your budget stretches to one stretch of the day only, cover the arrival and the standing-around-with-a-drink part rather than the meal. That is where a room goes quiet on its own, and one voice with a guitar fixes it better than anything else you could book.