We are members/coaches/speakers of the REIA group here in DE as well.

How can I raise the rent on the existing tenants without being the bad guy?

well I think you answered your own questions. pretty muchplumber for plumbing issues.. you might want a electrician to do a quick walk through of your panel and check each receptacle make sure he did not switch wires..when they really want to be bad they will put concrete down your drain lines.. so if he did not do that .. then your good there.. but you may want to snake your lines anyway just so you know there in good condition.As for the haul off.. what I would personally do.. is go rent a small u haul go to the home depot parking lot or where ever your day laborers hang out grab two of them and have them haul the stuff to the u haul then go to the dump and have them empty the uhaul pay them and take them back to home depo parking lot.. also have plenty of water for them or Gatorade and maybe a sandwich.. that's how I would handle that.

Buying in a bad area of any Midwestern city is gonna have a far bigger impact on the investment experience than picking one Midwestern city over another.Don't buy in the roughest neighborhood in the urban core.

Everyone has an opinion about legal protection, just like about dieting or economy.Here is the bad news.

Happy to see that you’re getting things going, and a duplex in South City isn’t a bad place to start!

Would it be a bad investment to buy a property in this submarket ?

The quickest way out of this industry is to have a bad start, so I'm looking for any tips that can hedge me if the market were to turn as I step in. 

This exact thing happened to my 4 plex but I got lucky, the storm was a month after I bought it and it was a bad storm.

They simply see the arrow point up on a chart, and expect it to continue in that direction in order to justify a bad investment lacking cash-flow.