Do I have them each provide me with $500 directly (check, MO, ACH) or have it run through 1 person or like a joint account for all $1500?

Unfortunately, you have a very good point @kevin m strong -- so many people use this as an out and it doesn't help in the event that a future tenant actually has a genuine health issue.

As far as what can you do with that money, I'm a big fan of investing in private mortgages or joint ventures. 

Up to 250k in profits single or 500k in profits if married filed jointly.  

We had opened a joint checking & savings account that we used to pay our lender from, thinking it would be easier to keep track of all income and expenses in a single, separate account.

You should layout a Joint Venture agreement that describes what each partner will be doing.

I would be happy to Joint Venture with you on this.

Louis, she mentioned they would be very interested in buying a property for me to live in and have joint ownership of while handling the property management responsibilities while being compensated for my time doing handyman tasks.

Hello everyone,My wife and I recently got married and have all our personal finances are combined (joint checking, monthly budgeting together, etc.).

Maybe they know there is one item that won't pass inspection and you can jointly hammer out a compromise in the agreement.