YMMV with higher short-term rates but fewer short-term visitors during these months.Also, Airbnb has started collecting hotel/occupancy taxes for Chicago now and I believe such "transient" usage is defined as any stays less than a month.

Rich Dad Poor DadRich Dads Cash Flow QuadrantRich Dads Increase your financial IQThe Real Book of Real EstateThe ABC’s of RE InvestingThe ABC’s of PMRich Dad RE Tax AdvantagesThe 10X RuleThe E-MythThe 4 Hour Work WeekBiggerPocketsPodCast -I hear #136 is exceptional!

E.

For that matter, Plan C, D, and E would probably be a good idea as well. 

Its a 2 bed 1 bath in the better part of V&E and should rent pretty high in that category.  

Real Estate Rewind Starting overhttp://www.biggerpockets.com/files/user/brandonatbp/file/real-estate-rewind-a-biggerpockets-community-bookGood Luck e legacyPaul 

I'm currently reading The E-Myth Revisited (Why Most Small Businesses Don't Work, and What To Do About It), and it's been an incredibly insightful read so far.

Cigarette smoke should not be quite that involved, but I would be careful.

I've been poking around the reading list (and of course read the free E-book), but I'm still looking for some more concrete guides to determining the value of REI specific to our situation.

turbo tax is designed for someone who owns maybe one or two conventual rentals and can not handle complex transaction like option contracts, because your asset is actually the contract itself which would normally be reported on schedule D and it sounds like your trying to treat as a rental property on schedule E.