If you are looking to build quick capital and another full-time job, then flipping may be the answer...if you are looking for a slightly more passive approach and looking to build that long-term wealth, buy&hold'ing is maybe a better strategy.I've found introspecting on where I want to go long-term has helped clarify my short-term path...The beautiful part is Chicago offers all options at affordable prices general speaking compared to other metro areas.

Consider capital gains tax, house hacking, FHA loans, and neighborhoods with high rental demand.

Paying above market to gain other benefits is sometimes a difficult pill to swallow, but for the unbiased investor looking for the best” ROI the risks and rewards must be analyzed rationally.  

Are they worth the monthly payments to gain access to Investor Names? 

Simple.Those that have value to provide will be incentivised by the BP readers to have value in their posts so they can gain exposure.

By qualifying as a real estate professional (REPS), you’d absolutely be able to offset your wife’s W-2 income with passive losses from your multifamily activities.

If the property is sold at a loss, can you unwind a 1031 to off set the gain on the sale of initial property?

Whatever your case may be, I will be successful with apartments as I've already started but I figured I'd reach out to gain a word or two and I am not pleased with the responses.

While real estate is more passive once stabilized, acquisitions can require more hands-on management.The choice depends on your goals.

What might help you for the next attempt is to read (BP's book written by yours truly--The Hands Off Investor), and network (join a community where investors discuss deals, trade advice and observations--coming soon will be Passive Pockets, an offshoot of BiggerPockets which recently acquired the popular passive investing group Left Field Investors).