I own about 40 props in Illinois and N Indiana and have been working on taking the next step... starting a property management company.

So practically it's likely easier to sell each one individually.

It’s all about taking that first step!

Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

This step will be key for further steps below!

If an investor can create a Texas Series LLC for $350 and place each investment property inside a separate series at a cost of $27 filing fee, why not take this step to ensure that the problem of one property can’t flow through to the other properties?  

I have decided to step into the world of property, curious to see what people here think of contract wholesaling.My main questions are:- Is it difficult to find investors after negotiating a decent assignment deal? 

Your first step will be to talk to several lenders to find out what you qualify for.

In your second scenario you would eliminate all capital gain and depreciation recapture with the step up in basis.there is no statutory holding period that qualifies you to convert the properties. 

Everyone who steps inside is wowed by the space and in awe of the 2-story wall of windows surrounding a 140+ foot redwood tree.