Basically I would not like the situation when I work with one arm of Chicago bureaucracy to pull permits while the other arm is sending bulldoggers to level my place.

What I love most about it is that you can tailor it to your financial goals.

From a purely financial return POV, cash is a smarter move than using debt on a lot of deals.  

https://www.biggerpockets.com/blog/wall-street-is-not-buying...Wall Street is not exactly the easiest group of institutions to defend, in large part because they most certainly do merit an enormous amount of criticism for many of the financial shenanigans they engaged in that helped contribute to the 2008 Financial Crisis, such as being bailed out by taxpayers only to give out exorbitant bonuses to their executives before needing to be bailed out again when COVID struck.

How would that affect his tax situation if at all?

However, specific regulations may apply, and it's advisable to consult with a legal expert or housing authority to ensure compliance and handle the situation appropriately.

(Before people jump on me, I know there are exceptions, especially multiple family situations, but let's be real.

Especially in real estate, there are situations where you might own something for a short period of time, but I think the main point of this statement is to make sure that you buy right in a way that is consistent with your end goal.

I tend not to provide financial advice but would say as I get older my risk profile will continue to decrease.

Luckily, the layout of the lot and the house makes this possible.Here are my questions for anyone familiar with this kind of situation, especially in St.