If cash flow is your priority, out-of-state investing in more affordable markets like the Midwest or Southeast might make sense, though managing from a distance requires a solid local team.If you stay local, networking will be key since the best deals in expensive markets rarely come from the MLS.

I don't know anything about their policyholder experience.However, every homeowners policy I've ever seen, even with a "home sharing" endorsement or rider, requires some owner use of the property. 

If you can qualify for conventional cash out refinancing, most lenders do not have a minimum loan amount requirement.

Some of the new laws in the state house will require you to provide Air-Conditioning.

Effort is still required to communicate with the Craigslist advertisers, but having software to lift the deals out of Craigslist would surely be worth $1,000. 

May require some patience, but trust me, this stuff is not easy for some people to follow... 

Are we required to pay FICA tax on the deferred income? 

In Illinois for commercial property, property disclosures are not required. 

In addition, the Grantor will probably be required to sign the same seller's affidavit that are needed for a non DIL closing. 

If you're an accredited investor able to meet the minimum commitment amount required by the fund, I have to imagine you have access to opportunities that are more favorable to you as an LP.