I have moved away from my W2 job and living off of investment income (rental + stock portfolio).

Both can offer tax perks if you use the money for home improvements.

Sure- get a full time job, buy a small multifamily, live in one of the units and then repeat that process every year for the next 10 years.

Conversations with investors reveal that even those earning six-figure salaries face substantial pay cuts when changing jobs, often by 25-50%.

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.

So, I can keep my high paying job going and I can keep saving for down payments.

I'm looking at the different property management platforms and wondering if there are any that people LOVE that does all the property management stuff but also does a good job tracking the financials? 

I would if I were you, get contractors to bid the job from licensed and non-licensed contractors.

You could have sent him to collections and this would destroy his credit, which could impact his ability to purchase a home, qualify for a car loan, and possibly even cost him his job.

These spots have been getting more attention from investors and can offer solid cash flow while still being in communities that are seeing improvements.