I purchased a property that needed a lot more work then intended.

So, the prosecutor tries to charge something he can win on and that is typically related to something the buyer has done improperly in the purchase, possession or disposition of the property. 

Why do you think purchase contracts are so long and have such small print?

This property is cash flow negative at purchase.  

Ken’s questions should be foremost in considering the purchase.  

Are you wanting to purchase in the same area of Chicago?

You may get better results by purchasing a duplex, triplex, or fourplex.Here's a guide that describes what good cash flow looks like and how to analyze a property.

Quote from @Jonathan Snider: I have been saving up for a while to purchase my first STR.

It is in my book (available in January) and the score sheet is part of my forms package available for purchase.

I work with several real estate developers across the country and they all do it differently.My suggestion is to find a property type and an area/neighborhood/city/market that you are drawn to and plot your course from there.As for the amount of money you'll need, it's gonna be mostly driven off the purchase price of the property.