That is enough to hurt him substantially, but he is able to bounce back over time if he works at it. 

I've taken a look at some houses on the MLS (via Zillow, etc.) and found a couple properties that could potentially be gotten for cheap, but would need a substantial rehab.

In my experience, office property is generally better taken care of by tenants, and usually comes with substantially less drama and BS than apartments with 50% sec8 tenants.

In reality my house was substantially nicer, and it showed selling for $207,500 after only a month, while his sat for 4-6 months.

Many of these neighborhoods have flooded multiple times and, in talking to our insurance company and some of the prospective buyers for our home, FEMA can substantially raise premiums (think 15k year) and substantially drop coverage (eg 10k coverage) for some of these areas that chronically flood.

As a CA resident, I'm obligated by FTB Section 23101 - it basically says: "If you live in CA, and you do substantial work on behalf of an LLC that's based elsewhere, that LLC must register in CA and pay $800 per year."

That can be substantially more tax than folks think.  

If you do invest in Springfield as a long-term play you won't suffer in that you will make substantial returns even with evictions and vacancies just because the cost of entry is so small compared to the rent.

At a 10% to 15% deductible, my buildings would have to sustain substantial damage or completely collapse before I saw anything from the insurance company. 

@Varun Parkash Unless I'm misunderstanding, you will not be saving $300 in P&I -- If you are refinancing 10 year arm @ 2.5%, your payment will increase substantially.