Hi @Tim Holt I think in general house hacking is usually a good move because it gets you off the sidelines and into the game with the most favorable financing possible (30 year fixed).There's a lot of value in getting started today vs waiting some undefined number of years until conditions are better, which could be a long time from now, because real estate is a business and the sooner you start actually learning about that business, the better.With all that said, I always recommend that people analyze any potential house hack as a pure investment that they aren't going to live in, because someday they may want to move out and you should know up front (before you commit) whether you're going to be able to do that, or whether you're overpaying and will be stuck in the property unable to move out because it'll be cash flow negative if you do.So you had it exactly right when you wrote, "the property would need to cash flow when I move out and rent out all units."

I've never heard the 25% thing before, but any difference between FMV and sales price would technically be considered a "gift" with potential tax implications for your parents.You can avoid most seller costs as there's no reason to use agents in this case.As an FYI: I always recommend avoiding a FHA loan, if you qualify for a low-down payment conventional loan.

Connecting with local investors would be my number 1 recommendation.

Sewer issues in Chicago are very common which is why I ALWAYS recommend / almost require my clients to get them done + if there's trees in front or in the back of a property, there will almost always be plumbing issues + needed rodding. 

@Julie J.My recommendation would be to wait until you can afford a home with traditional financing.

Whatever the engineer recommends do, the longer you wait the worse it gets. 

I'd recommend finding local meetups as your next step. 

There are a couple of DIY cost segregation companies that provide you a questionnaire to complete to generate your report.I normally recommend a home inspection and appraisal in hand when completing the questionnaire.The completion of the study is instant.Best of luck.

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.

The bigger the reserve the better, obviously, but generally most recommend a 3–6-month reserve.Makes sense, thank you!