Your concerns are justified. Most likely you will find you have voluntary workers insurance, but the amount claimable will be very limited against that part of the policy. Ladders are a great concern, people falling off ladders can cause debilitating injuries or worse. There is too much risk involved for anyone who volunteers, and ambulance chasing lawyers could soon be on the scene in the event of an accident. It is my strong view that adequate funding through levies should be maintained so that the property is kept in good order and condition. You’ll find that working bees are attended by the same few people, many of whom may be limited in their abilities, whilst those most able to afford the cost sit back and do nothing, benefitting from the efforts of their fellow owners. Sounds like a classic case of insufficient funds provided in the sinking fund for foreseeable and necessary ongoing maintenance. So for a quality job go for a reputable painter carrying insurance, if the funds aren’t there it may be necessary to raise a special levy or borrow funds.