@Gregory SchwartzThe answer starts with an honest self examination and assessment. 

With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

An LLC shields personal assets from business liabilities, while S-Corp taxation allows you to reduce self-employment taxes by taking a reasonable salary and distributing remaining profits as distributions, which aren’t subject to payroll taxes.

@Anthony Zotto - By the way you ask the question I assume you're going to self manage the property instead of using a property manager.

So often rentals don't have taxable income; and once they do it's still not subject to the payroll taxes paid by W2 wages or on self employed income. 

@Kyle McVay I self-managed my first 5 units and then transferred all new units to a PM.

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

I want to remain local in NJ or at most drive down 1hr to PA (self-manage or, last resort, hire a PM)However, I must also consider maintaining reserves, a safety net for my primary home, and an emergency fund.It's just hard for a new investor now :(

If you are going to self-manage, you need a great TEAM.

Im not sure if I will hire them to establish the LLCs or do it my self, if I hire them or another company will be to establish one in KS and one in MO, then technically "copy and paste" the forms to establish the other LLCs.