As my first multi family buy - I think I was lucky to get into a 3x 3bed 1 bath multi family in an A+ area which immediately appraised for 100k above purchase price. The immediate need and plan is to live in one, rent the 2 others (3, if counting non conforming basement unit).

What I'm really trying to do is build a model for a plan of attack over the next 3-5 years, with rehab starting in the spring of next year, when I'll be without tenants. I've got a full time job elsewhere, and want a modern, reliable building that attracts reliable tenants in a good area while thinking about this from an investor's POV.

Goal 1: Build and live in a premium unit for myself. New kitchen, bathroom, floors, trim, laundry.

Goal 2: Address HVAC - boiler heat on my dime is $350 a month vs. passing off to tenants. Window AC units unsightly, and would love to get rid of radiators for personal unit.

Goal 3: Ground floor conversion to duplex down. Would like to remove liability of non conforming / rough basement unit by adding one more bathroom and bedroom, increasing value.

Goal 4: Optional - Revised kitchens and bathrooms for more desirable rental units and giving everyone in unit laundry - currently in basement for entire building.

Some questions:

1. Is starting in the early spring with a plan to be reasonably done by summer an attainable goal? 3-4 months of work

2. I've seen folks say ROI on ripping out boilers is not there - but I'm stuck between systems of wanting something modern for myself while the rest of the building is in between boilers. If the entire building is empty, that's the easiest time to do it, especially while working in the basement on the duplex. This is probably my biggest snag - "nice" units with window AC/ & heating on my dime is a detriment to rent - but also definitely don't get the monthly ROI by just doing my own unit and having two systems in the building.

3. Is there risk in adding a kitchenette in the basement so that it could be used as an airbnb - but really is connected by the front door of unit 1 if ever I wanted it to be a dedicated duplex?

Chicago, Illinois

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