Hello Josh,
im pretty sure we crossed paths at Middle Percy Island, back in May?
Glad to hear you made safely from there further north ok. From your mooring location at Middle Percy, I'd say you would suit a shoal draft or a catamaran?
But seriously the budget you quote gives you plenty of options. You can look at a 10 year old production sail boat up to 40 foot, reasonably safe option for expected ongoing maintenance expenses, or a cheaper older boat, or a dearer better older boat. Modern sail boats are not always as motion comfortable, IE they move about more frenetically in swell, but they are responsive and sail well in lighter winds.
Imho I would spend up to maybe 150 k on a nice up to 40 footer, you will need the remainder of your funds to bring her up to spec. Check out the marina's At Airlie, look at the charter boats for ideas. Even most privately owned secondhand yachts will have marginal sails, a decent set will bring the boat alive. And here is where you will understand how much it cost to own a yacht, what I mean is the difference in price for the gear to suit a 42 footer versus a 36.
Cheers Richard