We have recently partnered with Outsite.co, one of the largest coworking/coliving communities in the world to handle booking and management.The property itself has appreciated and we are watching the market to determine the best time to hold a capital event.

Even including modest appreciation and equity pay down, the ROI is between 7% and 12% for a non passive holding (not good for an active holding)I can easily afford this level of negative, but do I want to?

Property taxes are important, sure, but they shouldn't be the make-or-break factor that kills a potentially great deal.I get that, but PT is holding me back from getting positive cash flow.

Chicago cap rates are lower then interest rates so what I see clients do is rehab to add a ton of equity/boost rents and then either just hold it or do a partial cash out to get back 1/3 or 1/2 the money in the deal which gives you a higher COC.

Sounds like you have thought out a lot of this, but maybe also hold a competition with a cash prize at your closest architectural and design school.Can you build it cheaper than someone like this?  

Screening tenants well and then a security deposit or credit card hold process in place will limit liability.

Build your home criteria based on investment goals, risk profile, returns desired, holding timeline.

Investment Info:Single-family residence buy & hold investment.

Upon calling a few banks, i am told that there is a minimum of 6 month holding period before I can do a cash out refi.

We plan to hold for at least 5-10 years and likely 1031 exchange into something larger or land.