What is the best way for me to approach the conversation so that both parties can have a win-win?

I met with a potential client for an addition and during the conversation investment properties came up.

I will discuss it further with the contractor to try to see if his insurance will cover.If I call my own insurance and discuss this, but not formally file a claim, would they still take and note that conversation as a claim?

Love how you want to seize the opportunity...Hard to give advice without knowing more details about your specific situation, but things you may want to consider: 1) Take a deep look at the numbers, whats the property currently worth, how much would the renovation cost, whats your ARV, how much can you rent the place out for, what will be all of your other expenses, etc. 2) What would be your ROI if you move forward with the conversion vs if you made an investment elsewhere? 

Nothing says illegal conversion like 100% shared utilities...

But in case they don't read it the prescreening script should be part of your initial phone conversation prior to scheduling showings.If you have a hot property you can also schedule multiple people at the same time slots, creates a bit of a competition between them.

You should be getting out to properties early, your agent should have conversations with the agents to discern what the interest is, you should be discussing other tools to use to get noticed in competitive situations.I get not wanting to overpay, but paying over asking price is not always overpaying.

To be honest, I am disinclined to take the work myself as I am quite busy, however I have done day conversions and have built tiny homes.

My wife and I are new investors that got started about a year ago from a conversation with a couple of friends.

From a sales perspective, I believe the conversation would be more like how much cash would it take them to leave.