Also when you are under contract and get condo docs, make sure to read the meeting minutes (for the past year if available) they will indicate if there are any talks of an upcoming special assessment (which you don't want).

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

As noted, if your options are Reg D, private offering vs fully registered public offering, even if you are talking Pink Sheet (OTC) stocks, you have public filing costs, annual audit requirements, and likely more on-going expenses that have to be covered by the property(s) owned by the offering.  

If you tell the constable that you are concerned about damage, they may talk to him about leaving responsibly.If you are concerned about violence, have a means of defending yourself and let him know it.

Let's talk roofing. 

Getting that first property is exciting—and yeah, NYC is no joke when it comes to price of entry.Honestly, a lot of people I’ve talked to in your shoes end up finding better opportunities just outside the city.

If you consider Pittsburgh in the future I'm happy to talk about the market and help you get set up. 

Im hoping to find an investor to help me buy the lot next to mine so i can move up from doing tax deeds.. if not i have my next lot picked out and will continue to invest in them while i fix my credit and learn more on investing.. i have always wanted to be successful in life but drugs and bad choices have kept me from it.. now im proud to say there is nothing that will stand in my way of realizing my dreams Just following up.

The person said they would be willing to talk to me about the house in a few months.

The key would be making sure to talk to a local banker that can do CRE loans for owner occupied properties as not all banks do them.