Our aim is to maximize appreciation and rent growth while still cash flowing enough to break even after all expenses in the short term.

A great way to get started if you currently have a W2 job is to buy a house hack like a duplex or a fourplex where you can move into one of the units and continue to rent/manage the other units.

I'm considering partnering with a non-profit that would manage the sober-living program; with me just providing the house passively for rent on a per bed basis. 

What rent collection software do you recommend and why?

Fully rented property since listed for rent in May 2020.

I was broke enough that I couldn't afford rent at my apartment, but fortunately my landlord didn't notice, thanks in part or in whole due to some substance abuse issues.Anyways, when visiting my mom in the neighborhood where I grew up, I had noticed this construction van at a house on our street.

Currently situated in San Diego and can only afford rent for now because house prices in SoCal are bonkers.

I've been through situations like this.Hopefully the family pays rent and this becomes a non-issue.If they don't pay the rent, you need to be understanding and kind, but firm.  

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.

Property management can be great if you are willing to give up a percentage of your gross rents to not deal with headaches, but it's not like you can just ignore your asset.