Looking for positives and negatives based on experience...

This method obviously requires me to have positive cash flow (which I do). 

I know that Chicago has it's fair share of economic and political issues, but it's also a big City with a lot of positive aspects. 

With property taxes and the high cost of insurance, positive cash flow at today’s prices is a rarity

Hello, I am also taking action and just starting out in Columbia, SC.

It's a complete re-positioning.

Probably not 20 house, probably 10 is more realistic...P.S. people on this forum are very smart, caught my miscalculation really quick :-) I hope one day I will be like you guys when I grow up as an investor :-)Ok, lets say you buy not 10-20 houses with it, but 5, which is also will bring you 1.5k-2K positive cash flow, but those houses are in the middle of nowhere...

In my market there are plenty of options for positive cash flowing properties within the budget.

Positive and negative experiences welcome. 

@Robert Davis IIIOut of state is a great thing, if you live in California :-)It is defiantly doable, I know many people who have their entire RE portfolio out of state or out of country...Now , with all that said , if this is your first RE investment then for sure you have to visit the area, and get the local insight, plan your trip ahead and have everything lined up:Several "potential" properties that you would consider investing in, tour them real good and grade them for yourself ..When you visit these subject properties make sure to blend in as much as possible with locals , neighbors, mail man and everyone in town that will be happy to discuss and contribute REAL local insight ... at this point I would not take advice from anyone that is talking from position...