Otherwise we manually put external leads on the Ylupo drip which keeps them coming back.

With so many local and external variables, if anything is certain, a good deal on US real estate is, and there seems to be a growing window of actualization for the prudent investor. 

The transactions it facilitates impose externalities on the neighborhoods.

For external systems you can use Webhooks or Zapier.   

You may want to look into trusts based on what you're describing.Either way, I think personal improvement and working on financial literacy and responsibility will elicit faster and longer lasting change in a person than an external force requiring saving and doling out punishment if the rules are violated.

For example if you have a 12 year old property built to the prevailing trends 12 years ago you will have an Express that is a little more country style in appearance both external and internally.  

Condo ownership tends to be a bit easier than a house- usually the common area maintenance, like snow removal/lawn care, and external repairs(roof, facade) are handled by the condo board.

If you accumulate enough of them with leverage, you could create a real estate rental loss that could be offset against your income through the Real Estate Professional designation should your wife show 750 hours of management activity without external help. 

It is easy to manage as it is a condo and the maintenance fee covers all the external maintenance of the property.

Most commercial leases are structured as net leases: with multi-tenants, the only thing you should be on the hook for is property tax, maybe maintenance for common areas or external spaces.