Spend your time and money learning how to avoid that kind of situation rather than learning from on the job training.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I own 4 two/three flats bought between 2013 and 2020 in Forest Park, Illinois, at low interest rates and prices in 200000's  They cash flow nicely and prices have increased a lot. 

Quote from @Matt McNabb: I'm a solid $400k/yr job in NYC and have $250k to begin investing as my first step into building a portfolio, although I don't have time to be a landlord so I have to account for management fees.  

It is a nice safe long-term spot if you're approaching it with a more long-term traditional real estate mindset.  

But it would be nice to have an option to uncheck that box this time around since they're already in place.

Misjudged the job cost (contractor error, usually results in asking for more money)2.

Nice try, but this time does not count.In order to meet 750 hours, your wife will need one of the below:- do something else real estate related, like wholesaling or realtor- actively work on expanding your rental portfolio - have an extensive DIY rehab, like a month-long full-time rehab (and then she might need another kind of rehab)- a calamity such as multiple properties damaged in a storm where she will have to deal with insurers and contractors- something else out of the ordinaryAgain - if all you have is 9 single-family properties with stable tenants and typical occasional maintenance - you don't have enough work to collect 750 hours.

As an employee of a MF Development Company, your boss will expect you to dedicate full-time hours to your job.