I am currently challenging my property tax assessments on my residence so I am very familiar with this essential process for owning property in Illinois.

Okay, there is no equity above the first, so your note is worth essentially nothing.  

Liability protection isn't as big an issue in my homeland as it is here, as it's essentially covered by insurance and instances of law suits are far less.The IRA house of course has it's own in-built protection - I'm not even sure you could place it in an LLC on the basis of that status.The other point we also need to consider I guess is the liability insurance for the properties.

Unfortunately I also own my own small business as a musician and my write-offs essentially screwed me last year for financing.

Let's say a year goes by and you don't have any vacancies or repairs, do you start to draw money out as investment capital towards the next deal (essentially adding to net cash flow)?

Kiyosaki says a couple times in the book that essentially as soon as your free cash flow from investments equals your monthly expenses, you're virtually free to quit your job and go full time, as your investments can sustain your lifestyle.

Essentially its a numbers game, make enough offers and eventually a few will stick.By the way when you are calculating out what your offer should be (hopefully based on net income), take into account whether it's a total cash deal or, if you are financing, at what LTV and what rate, and take this into account when calculating out what your offer should be.

We had an early 20th century bungalow whose downstairs was "updated original" and the upstairs was essentially just a large loft.

You are essentially housesharing and renting out rooms and use of some common areas.

I know there are hard money lenders out there that will essentially lend you money based on the deal and not on your credit but from what I hear it can takes months to secure capital via hard money lenders.