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. 

recommended steps 30, 60, 90-180 days of getting my realtor license 1.

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? 

I've discussed with the county phasing the buildout in 2 steps, building 2 units at a time. 

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.

Here are a few tips as you step out on your own: Attend local REI meetups and events in DFW to connect with other investors and contractors.

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.

Not so much for step by step guidance but for "check in" to make sure there's something I may be missing (or have incorrect). 

I suppose I am grateful that there even was money to leave in the deal and that I have flexibility on what my next step is. 

I think deciding on a market is a really important first step.