Can anyone offer any advice on lease structure and insurance requirements to get this started off on the right foot to allow for a win-win for all involved?

As an out of state investor this has been helpful to get some insights from 3rd party sources. 

So trying to collect the $15.00 nuisance fine would open up a whole can of worms.And a year ago, the city here introduced recycling food scraps, involving another can.

Hopefully my comments help and I don’t come across as a party pooper.

My question is about the loan or mortgage - when people go into an agreement like this (assume they are splitting all costs equally), do both people obtain a mortgage for 50% of the property, or does one person get the loan in their name for the full amount and then just receives payment from the other party for all expenses, etc?

It kept him involved and committed because he had money coming when we sold the property.

I've been involved in this type of process a few times feel free to reach out.

There plenty of other opportunities elsewhere, my clients are involved in institutional grade properties across the country.

Your ability to speak to 'why it's a good investment' will rest largely on your ability to explain the numbers to both parties.

There isn't one right answer to that question--it will be a negotiation and is dependent on context and the relationship involved.