Even if a title company were to manage the setup making sure all parties are paid, the cheap debt and cash flow would not be enough to be enticing to any investor even if midterm rental could yield a healthy return. 

Refinance into a debt service loan.

Partner Driven’s expertise in market timing, combined with Archie’s local insight, ensured a fast and efficient transaction.

Eliminate debt, establish a budget, and save.

Eliminate debt, establish a budget, and save.

If you want to combine two or more lesser sales into one higher purchase that is fine as long as your purchase meets the timing requirements for each sale.  

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

And while yes, no one has the same pricing (combination of factors), I also continue to check on a regular basis our rankings and how we "present" on total costs per stay vs. our competitors.My gut says there is price creep and we might have a ways to go before the market really corrects.

We use a combination of HML and our private investor network.

I think your goal of getting your first RE investment for around $50k is doable as long as you plan to leverage debt (Loan).