If we had just paid her the others could have challenged.

Instead, focus on learning their plans, challenges, and openness to selling.5.

This may be part of the reason why some decide to quit pursuing real estate investing, especially when challenges start presenting themselves.

Challenges?

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

It isn't really any harder to drive a stick, just different, but for people who never learned it seems very challenging.

Any syndicate that over-leveraged and/or has a near-term maturity will be very challenged to survive. 

.: Hi there,I have an investment property in Atlanta and over the past year, the property had major challenges due to squatters.

An eviction will make it challenging for her ever to find a quality rental in low vacancy areas.  

many houses in the midwest, for example, are very old and need major rehabs.i personally think out of state investing is more difficult than advertised, and much more difficult in the current investing environment, with: prices high; interest rates high; tremendous demand for inventory, by both investors and retail buyers; and good PMs, contractors, etc. booked up.here's a really thoughtful thread with the experience of another CA investor and lots of different responses:https://www.biggerpockets.com/forums/12/topics/1215726-break...and here are some threads about how it can very easily go wrong:https://www.biggerpockets.com/forums/48/topics/1159104-overl...https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1160450-run-i...https://www.biggerpockets.com/forums/48/topics/1137397-balti...finally, you also said you "don't have a lot of money to start with."