As a PM, his team would be familiar with areas and could help underwrite the property and take care of the day to day headaches. 

When purchasing a small multi family property as a primary residence.

We are looking into getting a fixer upper and plan to rent out our original residence ( Zillow says we can get $2700 median rent in our area ) while moving and fixing up the new house.

In my experience, the average Section 8 resident behaves differently than the average market rate resident, and the government-backed rent is not worth the added hassle.  

I am looking to buy a 2 or 3-unit home in NYC. I plan on renting a unit and probably getting a roommate or two in my unit to maximize cash flow early on. So far, the best deal I have been able to find is 5% down with ...

Personally If you like your current residence and hope to stay there long term I would forgo major improvements on my primary and use all investment savings to make you more money and cash flow. 

With careful planning and consistent effort, you can create a portfolio that aligns with your long-term goals.Good luck!

Most of the FN moniker is for folks with no nexus or residency/citizenship to the US.

I really wanted to convert the residence to a rental property, but everything I have heard about doing so in Cook County has been very concerning.

Must have solar, ev charger etc.My materials distributors are expecting more inflation.Homeowners insurance is still going up.I wholly expect CA residents to continue to move there (wished I'd bought there!