I ran the numbers and am looking for some feedback on if this is a property that I should "pull the trigger on" so to speak.

Any information on how I can approach this here in Chicago, would be extremely helpful.

Units will be inspected once every four years, and complaints will trigger inspections in between.

My old school dad was extreme, but he'd say if he saw you out at the bars smoking that he'd kick ya out.

I'm just extremely thankful a friend suggested this site, but I didn't realize I had so much to learn.

But I’m extremely cautious when looking for flips or buy and holds.

Something that has been working for me so far is listening to all of the wholesale podcasts from bigger pockets including some on the rookie wholesale podcasts that can be extremely motivational. 

My DTI is extremely low ( under 5 % ) I have a feeling based on my income and minimal debt that the bank would lend me upwards of a 750,000 $ or more.

I believe there is a way to do this yourself, but I would absolutely recommend NOT doing that is it is extremely complex.

If it's your first project that can be extreme high risk to a lender and also to LP investors.