Whenever you have a W-2 job that offers a 401(k) plan that matches contributions, max that out.

In terms of structuring, an issue that has come up is how do we handle the transition from holding one property to holding several, especially if the members of this business have varying levels of capital to contribute at different times. 

That is the very definition of "highest and best use" and will make a lot of folks $$ while also contributing 8 affordable units to the city of Chicago.

You may not even need much money down with a FHA, VA, USDA loan and a seller contribution addendum.

Did each of you contribute the same amount to the partnership and therefore are entitled to split the income/ deductions accordingly? 

Or what other factors would contribute to a corporation selling a property that is making them money (or at least should be on paper).

contributing factors; current home loan is roughly 500k. being my first home it feels like a lot and I’m a little nervous to hang on to it.  

Partner with a local investor and find ways to add value without contributing capital (e.g. repairs, collect rent, analyze deals, research new markets, take pictures of properties, etc...) 

I have held internship positions at 4 different real estate firms throughout college and am willing to contribute my knowledge and skills to your business 😊

in general contributions into an LLC can be done without a tax consequence.