Their depreciation does NOT start all over again, but by trading up in value they have acquired additional cost basis that can be depreciated. 

The issue you have with mutli-family in places like Palatine is that the availability is very low, so they trade mostly off-market and are passed down to families.  

Many of the older investors on BP would trade places with you in a nanosecond.  

If you don't have a preference to keep the home, then a house hack is going to free you up to start scaling faster and grow your portfolio, but you're trading some convenience.This is the process I walk through with all my new investors. 

I enjoy my work - I am a mechanical engineer by trade and am a senior manager currently - but I have always felt a draw to own my own rental property.

Many investors are scratching their heads wondering why certain asset types have been largely unaffected and, in some cases, even performing better and trading at higher prices than before the pandemic.

Keep the ones you like; trade out the rest.

I am a psychotherapist by trade and work with veterans.

Did you ask for a cost breakdown by Trade Category?

Chicago is such a great market to invest in, and you will be well positioned as someone in the trades.