Chicagoland is extremely tenant friendly so understand that going in. 

What's a friendly foreclosure process?

A lot of the cost is associated with the drive to get out and back to our lake house.If your friend isn't listed on VRBO, she is missing out on revenue and bookings. 

Great to hear that you are exploring your investment options and learning about the different options you have.

I started using both at the same time and found AirBnb to be far more user friendly with less clicks/swipes needed for any task.

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and it's super landlord friendly (so you will never have to go through a 12 month eviction or anything close to that!).

As I learn both options.

As Guadalupe said above, a DSCR is a great option for buying with a lower DP but it comes with the caveat of higher interest rates; and as Nate said, National Bank of Coxsackie in Glenmont is a great local bank which wont sell your note to larger banks.

I have a friend that buys and sells quite a bit in SoCal.

I'd estimate that I currently have about $300k in equity on my home, and am seriously considering borrowing some of it to invest in real estate, however I have no idea what the best options would be (syndicating, rentals, flips, lending, etc).