I wanted to create an STR experience and bring my bold ideas to life.

I'm not sure what you've heard or are expecting, but as with anything in life you generally get out of it what you put into it. 

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. 

I understand they can make our life a lot easier but is it worth it if it eats up a lot of our cash flow? 

I wouldn't bet my life on 50%, but I would bet they are more problematic than the typical long-term renter.

There is life stages to investing, and the math is clear that strategic debt use, strategic leverage, pyramiding, appreciation, is the wealth generator. 

He has lived here his entire life, and knows the area very well, and he is a general contractor and has been remodeling homes in our area for 20 years.

By building strong connections and sharing knowledge, we can support each other's journeys and uncover new pathways to success.Moreover, let's not forget the importance of maintaining a healthy work-life balance.

The tenant laws in New York make life as a property owner way harder. 

Where do you want to be in life in 3-5 years?