House hacking north side of Chicago - 24 years old, am I ready?

[Brett Lofendo]

24 years old, single. Living with parents in Chicago suburbs but moving to Lakeview East (North side Chicago) next month to get a feel for living in the city. Current salary 110,000 hybrid tech job. Savings of 50k in HYSA @ 5%. Student loan debt of 40k, paying 700/month (20k at 4% paying 200/month and 20k at 0% paying back parents 500/month). Drive a 2009 car that is paid off.

I'm taking this next year to rent in Chicago (rent is about 1600/month) but am starting to seriously think about house-hacking and want to start talking numbers now so that I might be ready to close about a year or so from now. Are my finances in the right place to be starting house-hacking soon? I've heard that it can be difficult to house hack with FHA loans especially in HCOL nice areas (where I'd prefer to live). But, I think my financial situation may be good enough to do a 5% conventional loan, please poke holes in my plan if there are any.

With the north side of Chicago as my market, I think duplexes and 3-flats are what I'm mostly going to be looking at. Does anyone else have recent experience in this market and could share their story? I'm just not sure if my situation right now is good enough for go-mode. I do have the option of moving back in with my parents in the suburbs a year from now if I need to save up any more capital. Our suburb is pretty far from the city, so I wanted to rent in the area for a year before deciding to buy anything in the city. Thanks so much, have already learned a lot from this site but looking to get more personalized advice.