Go the tried and true conventional route (for either flipping or buy and hold), learn your lessons, understand your value, and then use that to find the private investors who might make things a bit easier long term.

It's doable as a market to do what you want, but you must understand the block dynamics if you are going for Chicago proper.

@Peter PeterMy understanding both are prohibited transactions.

Learn more about REI, understand the market around you, then buy deals that match the strategies you want to pursue.

It's crucial for all partners to understand the implications of personal guarantees before committing to them.

As a broker in the transaction, you’d want the principal party you represent to sign waivers acknowledging their understanding of the significant risks they’re undertaking.  

@Jon Kim it's a very interesting question if I understand it correctly. 

So, I think many investors know enough about the possible issues from their own experience to do some research themselves and then understand the possible risks and are prepared to deal with them.

And I understand you also probably lost EM is that True.

Trying to understand if we should sell now while we can still avoid capital gains or should we hold property as the area continues to become more and more desirable.