.: 1st floor demo 4th pic: Bathroom & backrooms still standing pre-demo5th pic: 1st floor as open shell , all walls down & new sub floors 6th pic: Framing of 1st floor started GROUND/CELLER FLOOR: BELOW 1-2 pic : Pre-demo 3 pic.: demo (All walls taken down, a total MESS!)

Suggest you look up schools using https://www.greatschools.org

,You seem conservative in your approach and your $40k/year goal is so achievable in 5 years without leveraging up the wazoo like others suggested.

I think sending mailers to a specific group of sellers will be the best way to find off market deals with my criteria, and I am trying to learn the process and would love suggestions on search criteria that have been helpful when creating sellers lists, and what list broker you found most helpful.Oak Park, ILJefferson Park, ChicagoWicker Park, ChicagoBucktown, ChicagoLogan Square, ChicagoHumbolt Park, Chicago (nicer east pockets by Wicker Park)Hazel Crest, ILHomework, ILFloosmoor, ILTinley Park, IL"Northwest Indiana".. not that familiar to be honestWhere in greater Chicago am I skipping?

Developing a relationship with the students is key (mostly this just means leave them alone and let them do their own thing) because they will then suggest the place to their friend network when they move out/graduate.

@Mark Kao I would suggest talking to the property management company that covers the HOA first and foremost.

Canadians have a strong bias towards using Realtors and banks and generally don't know about the alternatives, so as a wholesaler there's not only the privacy issues, but a basic trust issue when asking a stranger to sell me their house.So Tiago, you suggest driving for dollars and just straight up knocking on those doors?

OR should I wait until next year and do both at the same time.Advice and suggestions are greatly welcomed. 

I'll check out the links suggested. 

I need to develop a Chicago team to make such analysis as you suggest.