@Will Gaston I have no experience with this particular situation, but it seem like you have to decided between an asset sale or stock sale. 

Should I invest in a Detroit and buy a cash house/duplex or use that money for a down payment in a better place through ROOF STOCK? 

I'm not a huge fan of the stock market, but I like the matched contribution and the tax benefits.

It's really hard to predict future impact on the value.   

The key for "tenant-proofing" is standard stuff, easily replaced and in stock, and durable without being fussy.

The other RE that may have money put towards it really is not part of the other RE refinance (other than the borrow chose to use the funds toward a different RE versus stocks, of mattress, or commodities, or bonds, or mineral rights, or ???

I’ve liquidated nearly 3/4 of my stock portfolio and recently acquired my first investment property - a duplex that is currently rented and doesn’t appear to require much work.

With all of these new apartments and lofts being made, it is clear that there is a prediction for the future on influx of students to this area.

The overall goal with this property would be to live in it for the minimum required time to qualify for the loan while renovating and as soon as all 4 units are finished and tenants are in line  I would either move out or start renovating the basement into a 5th unit which there are plans for but because it switches it from residential to commercial I can't do initially to my knowledge.Background info: Currently working a full time job 40-60hrs a week, making ~$500 a month in dividends from stock investments reinvesting it with a DRIP program.

it really follows the housing stock grade system as well if you have D and F housing you primarily have D and F schools. ???