You will want an operator that has a proven safety track record and is reliable
The good news for you is that being a fully licenced operator for several years now, we have a perfect, nil incident history. Something that is reassuring for you.
Of course we have insurance, not only to cover our drones but also any third-party liability. Imagine using someone who you know has a drone but not licenced or insured and something happens. If they have no protection then you could be open to all sorts of claims and litigation.
We conduct a risk assessment and JSA (Job Safety Analysis) for every shoot we attend. This is a CASA requirement and offers peace of mind to you knowing that we've considered all possible scenarios of the flight to ensure it is conducted safely with a minimum of risk.
You may require copies of risk assessments and proof of insurance (Certificate of Currency) and these are available to you.
Of course you'd like to be able to control everything but the main factor outside everyone's control is the weather.
The main limiting factor is wind.
How much?...well around 15-20kts is starting to get annoying, but we can handle it. Affecting the flight more is wind gusts which can make smooth flight very difficult. Rain is definitely an issue with electronics but water droplets end up on the camera anyway so it's pointless. If in doubt, then we put safety first and if this means not flying then we don't.