A tenant lost his job at the same time as his wife, I met with them and found out they had family in Atlanta thay could move in with, but didn't have the money to get there.

Martin the property management argument isn't really an argument if you look at the bigger picture that most investors don't want to manage their properties anyways because they are spending most of the time on their main job.

I guess my challenge right now is to define the strategy and balance all the factors, such as job and population growth (value increase), cashflow (demand & supply market, interest rate, property tax, maintenance cost), and risk control (insurance etc). 

This would be a tedious task to do on a daily basis. 

You have to be an active manager and many current owners are not wanting a second job and are selling.

The potential liability from having someone do a job they are not licensed to do far outweighs the cost-benefit.

However, in the case of safe unpermitted units there is a state sponsored agency (HCD) that is tasked with getting jurisdictions to comply with the various laws regarding providing housing units.  

You can tell who is actually passionate about their job and passionate about the market usually pretty quickly.

I started him on handy man tasks.  

If it's way out of whack with the market average, dig deeper.Debt Service Coverage Ratio: Key for nderstanding if the property's cash flow will cover financing comfortably.Historical Vacancy Trends: Especially in areas like Chicago, where local job markets fluctuate, knowing vacancy trends can help you anticipate rough patches.Rent Growth vs.