Pymble parties tend to happen on a lawn. Big blocks, mature gardens, a marquee hired for the weekend, and that setting asks different questions of an act than a function room does. The whole top ten is pinned to central Sydney, a fair run down the Pacific Highway or the M1, so every one of them is travelling to you rather than living around the corner.
They do carry a solid run of reviews, which is not true of every suburb on this site, and duos lead the list ahead of soloists and cover bands. That fits: a duo on a lawn with a small PA is the most common upper north shore booking there is, and the acts near the top have clearly done a lot of them.
Top picks are the nearby performers with the most visible reviews, then rating, then the closest; further afield the closest come first, and premium listings break remaining ties. Distances are straight-line from Pymble. Ask each act whether they travel to your venue and what that costs.
All ten are pinned to central Sydney, so you are looking at a drive up the highway rather than someone from the next street. In practice that is standard territory for every one of them and the upper north shore is well served. Just expect them to ask about parking and access, because they will be arriving with a car full of gear.
A duo or a soloist, amplified enough to carry across a lawn but not so much that the neighbours join in. Grass eats sound, so even a quiet act needs a small PA outdoors. Make sure there is a firm, level spot for them to stand and somewhere dry to retreat to if it rains.
They are real reviews left on the acts' original listings, with their original dates, and the Pymble list has more of them than most suburbs get. They are still not a ranking of who suits your event. Read a couple, then ask for a video of the act playing the kind of party you are actually throwing.
There is no stage, no power and no cover for gear unless you arrange it. Tell the act it is a marquee on grass and ask what they need, because the answer usually includes a flat platform and a nearby outlet.
Big blocks buy you some room, and the local rules on noise still apply once it gets late. Agree a finish time when you book rather than negotiating it at eleven o'clock with a band mid set.
The upper north shore runs a lot of school and community events, and they cluster around the same few weekends each term. If your date is one of them, book earlier than you think you need to.