Tasmania's venues settle this one for you. Sandstone warehouses on the waterfront, working cellar doors in the Coal River Valley and old halls out past Richmond mostly have hard surfaces, no installed sound and limited power, and a pair with a small system walks into that where a five piece cannot.
The honest warning is how few pairs take private bookings across the south of the state. Message most of this page in one sitting rather than one at a time, keep solo performers and small bands in view as alternatives, and give yourself more lead time than a city this size would normally need.
Top picks are the acts in this category in Hobart, without a review, rating or premium ranking: all these sort keys are tied.
You are paying two people, so the length of the booking leads, and loading in and packing down belong inside those hours rather than beside them. Distance out of the city comes next, then the question of whose sound system gets used. Give each act your exact timings and ask them to price against those, then read the starting figures here alongside the replies.
Give yourself more room than the population would suggest. The same handful of pairs field every enquiry for the good summer Saturdays, so six months is a reasonable run-up for a wedding between November and March. Take a weeknight or a winter date and the pressure disappears, often down to a couple of weeks.
Most will, and rural weddings make up a good deal of the work down here. The detail to nail down is when amplified music has to stop, since country properties often carry an early limit in their planning consent. Get that from the venue before you agree the hours with the players.
Up to roughly eighty guests in a home, a restaurant or a modest function room, two players with a decent PA cover it and leave floor space free. Bands make sense once you have a stage and a crowd big enough to justify one, and locally there are far fewer of those to hire than there are pairs. Ask how each duo builds the last hour, because that is where a two-piece has to earn its fee.
An evening set outdoors here can drop below what a guitar or a singer enjoys, even in the warmer months. Ask what the players need if the music runs outside after dark, and hold an indoor spot in reserve for the last set.
A booking in the Derwent or Huon valleys means real driving at both ends and a dark road home after midnight. That belongs in the quote, and it only does if they know the venue when they price it.
Players whose regular work is in licensed rooms may be used to a system already being there. A hall, a shed or somebody's lounge room has none, so ask what gear travels with them and whether any lighting is part of it.