I'm interested in buy and hold deals through the BRRRR method.

I have a few clients that have asked me about buying investment condos and I generally tell them to not consider it vs a house/multifamily

@Mark Peeples it's buy and hold and rent out to tenants as a mid-term rental unit.

We have started to think about selling the property and using the proceeds to buy another home in a more desirable area where we believe market and rent appreciation has greater potential for growth.

.- it is cheaper to buy a property with an existing ADU than adding one   In addition you would receive RE purchase financing.  

We have been reading The Multifamily Millionaire by Brandon Turner and are very 100% sure about buying a multifamily property as our first investment.

Cold outreach is all about volume because you are trying to find the 0.5% of sellers who are motivated to sell.If you are looking for leads of sellers who are already looking to sell, you are better off doing inbound marketing such as SEO or PPC, or buying leads from companies that run their own PPC campaigns, which are called PPL (Pay Per Lead).For PPL, I would recommend https://propertyleads.com/

Things like the roof…you can research right away and hire a roofing contractor to come out and fix /replace.

Can you afford to buy a new house without selling the Chicago home?

When you say be a part of the above point, do you mean buying up new construction in the area?