Don't be house poor or you may be houseless when the next downmarket, job loss, recession, or stubborn leak shows itself.If anyone is looking for advice on small software companies, or agencies, or balancing a startup during a day job, I will try to reply or answer DMs as best possible.

If I did decide to go this route, are there any pro tips anyone can provide on what I should screen for during the tenants application that is more specific to dealing with housing voucher applicants?

You can also use a software to do more accurate estimates on your own , once you see the property and know exactly what needs to be repaired and how you want it to be repaired.

- If you're in an area direct bookings are popular (Gatlinburg, TN for example) use a property management software that also builds a direct booking site for you.

Additionally the CRM has to be one of the buggiest pieces of software with the absolute worst support Ive seen in my adult life, so I wont name them here. 

@John Morgan what PM software do you use to self-manage properties?  

You can do this manually or through management software like TenantCloud and others.

I think she should Airbnb, she thinks she should go with these applicants. 

And, this should go without saying, but always defer to Fair Housing guidance, ensure you're treating everyone equally, and keep diligent records of all applications for 5 years.

In November I submitted my shared-housing application to Chicago’s BACP, with the hopes using my basement unit as a short term rental unit (Airbnb, VRBO, FF, etc.).