@Shiloh LundahlTheoretically assuming properties were identical in every sense yes because I don’t need cash flow and would rather have the extra $100k in equity.Now $600/mo could get you another $100k mortgage to get you another property that could potentially also cash flow but for me personally I am in equity play mode now income mode - just my personal choice but nothing wrong with the other scenario

Long story short, gives you a lot of options and depending on a value add play and negotiations, it won't take as much money up front that could be used for renovations.

Decide which game you want to play.

Decide which game you want to play.

Decide which game you want to play.

In my experience the Landlord / Tenant laws are less favorable in Chicago and I have concerns in how the budget deficit in Illinois is going to play out.

This is where the operating agreement component comes into play.

There are countless factors in play here and it makes answering this question or assessing cost very difficult.  

Even with a fence, I wonder if one could argue the bridge isn't an "attractive nuisance" because what child wouldn't want to play on that bridge even if they needed to climb a fence to do it. https://www.law.cornell.edu/wex/attractive_nuisance_doctrineSo, I would either remove the bridge while its a rental or add the the railings.

20% Factoring in property management we see breakeven at about 25-30% down depending on the deal.Appreciation has been 4-10% annually with variations of course.