what other alternatives can I pursue in looking for a deal out here in Chicago.

As an asthma sufferer, I too wanted to find an alternative. 

@Tony Wood, I don't believe you can view the MLS without a realtor or a license, however I would suggest realtor.com as an alternate.

like a Google Docs is there an alternative to QuickBooks ?

Because of this, I always advise tenants that unless they have family they can stay with on a temporary basis, they are safer to give their landlord 60 day notice than 30 days.  

Alternatively, look up the owners of local self-storage places in your area and reach out to them.Best!

It's safer and allows economies of scale. 

As a high income earner, there are alternate routes that garnish high returns than LTRs, are more passive (nothing is truly passive) than both LTRs and STRs, AND expose you too much less liability.

Alternatively, an engineer or architect could do the whole thing.

If you want to rent do you want current cash flow or do you want safer areas with more appreciation potential.Pigtown is the closest area to downtown that is still inexpensive but currently it is not very nice area.