A good question.
A local answer.

Check official market and event calendars for the exact week, then pack warm waterproof layers. A central base makes a weather-change day easier.

Keep the city-and-mountain day as a weather-flexible alternative. Mountain conditions can also change quickly, so check the official access notice before setting out.

Check toilets, seating and weather before departure, and keep a taxi or car return option. Leave room for rest rather than filling every daylight hour.

For breakfast, compare current menus and opening days within an easy waterfront or city walk. A bakery or cafe can suit a quick start; a booked restaurant suits a slower morning.

Book the tasting and dinner only after confirming MONA entry and return transport. Keep one activity optional if the flight is delayed.

Keep the first drive short after the flight and have water and supplies before leaving town. Free camping is only a saving when it is permitted and reachable safely.

Check street gradients, lifts and the walking route from the door, not just map distance. Hobart hills can make a short walk feel longer.

Choose the bar by atmosphere and seating as much as the fire. A small room can fill quickly on a cold evening, so check whether it takes bookings.

Confirm bookings, driving time and a designated driver if alcohol is involved. An indoor Hobart option is useful if the mountain is closed or visibility is poor.

Price airport transfer, city pickup and one-way return fees together with parking savings. The cheapest daily rate may not be the cheapest plan.

Choose scenic drives with short, firm-surface stops rather than tours advertised as easy without detail. Ask operators about boarding steps and the walk from the vehicle.

Check the street grade and kerb crossings between the accommodation and the places you will visit. A generally flat waterfront block can still have difficult thresholds.