I'm experienced in screening tenants, having co-signers, etc.

I do screen heavily, but fear that with less expensive properties it will be difficult to find "quality" applicants that can pass screening unless I greatly lower standards.  

I would suggest you screen this person as a new tenant and see if he qualifies.

Crosby, worth touching base with an attorney because tenant law can be so local, but that being said:You have the right to screen and approve the people that live in your property (adults anyway).

I saw the property the 1st day it was listed, while at the house speaking to the agent she literally was receiving offers for the house and the phone was ringing off the hook with people trying to see the property. 

So you screen them to find out as much as you can and make an informed choice.

Does anyone have advice on the best times to begin advertising, examples of leases in similar situations, and best practices for screening tenant-roomates? 

The return on equity is low and damage too costly if you don't screen well.If a nicer place I would explore selling it and taking the (probably mostly) tax-free gain and invest or otherwise use the proceeds for their benefit.As Ashish points out, heirs would inherit the house at it's current value at death whether it's a rental or not. 

Or use your lunch break at work to step out and make a few phone calls to network and build relationships. 

Now I carry digital copies I made of the rules with me on my phone and just fact check him everytime he speaks to me.