It's a night and day difference the tenants in an area like Logan Square vs small town C class areas. 

That said, there are different entity types that may be beneficial for a flipping business (LLC, S Corp, C Corp, etc.)For rentals, there is a degree of personal preference - some like to have a separate LLC for each investment, some use Series LLCs, some group a few investments in a single LLC until a certain threshold of equity is met, like @Tanvir Sattar mentioned.Although, I don't typically agree with that method because the investments within that LLC are still vulnerable to others within that same LLC.

@Ian C. that's so great to hear.

@William C.

Schedule C if you a sole proprietor) & you do not have any w-2 employees working for your self-employed business or otherwise.2.

Just remember if one thing doesn't work, just keep trying and always have a plan A, B, C, and D.   

The loop market is characterized by the following features: a) high-rise full amenity condo dominated; b) young professionals/students dominated; c) very active and strong rental market; e) fast turnover rate.5.

The web person would likely be an S or a C.

But lenders will want to see some experience and cash reserves in addition to underwriting the deal itself.1.c.

I'm interested in areas with room for growth in maybe a C+/B- areas.