Hi BP,Excited to finally be signed up for BP Pro, finishing up 'The Book on Flipping Houses' and have been on the hunt for a couple months now for a great first opportunity!

I read books, I visited other forums and I networked like crazy.

I have read the BP beginners guide to REI, I read RichDad/PoorDad, and currently reading Home Buying for Dummies.  

Not in my books!

Meanwhile start saving up for a down payment, networking at BP and Meetups, and learning with books and podcasts

The safe harbor applies to amounts paid during the tax year to acquire or produce what the regs call a “unit of property” (UOP), you must meet these requirements: (1) at the beginning of the tax year, the taxpayer has written accounting procedures treating as an expense for non-tax purposes amounts paid for property costing less than a specified dollar amount (which will be 2500 for you), or with an economic useful life of 12 months or less;.(2) the taxpayer treats the amount paid for the property as an expense on its books and records in accordance with its accounting procedures. ( do this on your bookkeeping software or whatever you utilize)(3) the amount paid for the UOP doesn't exceed $2,500. as substantiated by invoice.Note: The cost for the Unit of Property includes additional costs (for example, delivery fees, installation services, or similar costs) if these additional costs are included on the same invoice with the tangible property.Eg:A purchases 100 printers at $500 each for a total cost of $500,000 as indicated by the invoice.

I'll check J Scott's book, but any Chicago specific knowledge would be great.

I am looking to get advice on tax reporting and book keeping, I do have some accounting knowledge already but would like to learn more.

The answer to that question is to start by investing in yourself...with books, podcasts, and analyzing deals. 

I guess, because of that, my best advice would be to book yourself a tour of Airbnb's throughout the state.