This really depends how much you have invested on whether or not it's worth it and how much depreciation recapture he would be subjected to 

Depending on the contract negotiations, the buyer will likely want title insurance and may ask for you to pay for the premium, which is calculated at as $5.75 per thousand dollars of the sales price up to $100,000 and $5.00 per thousand dollars of the sales price thereafter up to $1,000,000. 

Chicago's market varies, so $500k-$600k might get you something nice, depending on the area.

@Carlos Ptriawan Ah… I understand.It depends on the jurisdiction.

Theres also many local real estate meetups depending on how far your willing to drive where you can meet other like minded people and network to learn from them as well. 

Where you look might depend on your answer. 

Depending on the seller's situation and desire they may/may not be willing to negotiate this.

Figure out what homes sell for (depending on their condition) and what people are willing to pay for them including how (i.e. cash, financing, etc). 

Depending on the cost of the job (or the cost of them really messing it up), it's worth considering for sure. 

@Sage Sager-Romanoa lot of this is going to depend on the work and effort you are able to put in.BRRRR is very difficult and very labor intensive.can you buy something in Texas now and keep renting in LV?