How big a project is TOO BIG for a first timer / 203k?

[Colin Hudson]

I'm a first time buyer looking for a 3-4 unit property to house hack in Chicago. In the neighborhoods I'm targeting, buildings that would meet the FHA guidelines (i.e., ~$566k for a 3-unit and ~$703k for a 4-unit, including renovations) need significant work to achieve market rates. I'm comfortable taking on reasonable renovations on a per unit basis: taking down walls to re-position the unit, new kitchens, updated bathrooms, new floors, etc. My question is, when is a project too big? 

One property in particular I looked at (potential for 4 units, with 1 in garden/basement plus 3 above-grade) would need all the standard rehab stuff, almost gutting down to the bones, plus 5 major projects:

1. The entire rear addition is unstable and needs to be removed/replaced  (about an 8-foot deep wood staircase with landings and entrances to each of the 4 units, plus extra space for ~60 SF per unit). How much would this demo + rebuild cost? I'm assuming that the zoning allows for reasonable extension on the back of the small-ish unit, so I would be looking to add a full staircase and ~100+ SF per unit 

2. The roof of the building is currently a triangle peak, making the attic unit unmarketable. How expensive (and reasonable) would it be to square off the top floor so that the roof is flat and the top floor unit has the same footprint/space as the other units (i.e., not 45 degree walls!)?

3. The basement unit looks pretty illegal, given its low ceiling height. How expensive is it to dig out a basement floor unit to meet code?

4. Since 2 of the units are likely illegal, all new metering is required throughout the place (I'm assuming this can be done not only for electricity, but also for water and gas?)

5. New centralized HVAC systems would need to be installed 

Typing out all those projects as a first timer was pretty scary...I can't imagine actually taking this one. That being said, are these initiatives achievable? If so, at what rough cost? I would love any insights around any of these initiatives, just so I can start developing a better eye when I'm looking at these fixer upper properties for my first house hack. Really appreciate any input you might have! 

Cheers,

Colin