Stay away from Chicago unless you are required by your employer to live in Chicago. 

Piercing the veil is very common. 

@Joshua TalamanteIt is actually not that common for Solo 401(k) bank accounts to exceed $250K in cash for any extended period of time.  

In the apartment industry, typically $250-300 per unit per month is held by the banks in escrow, but R&M can be much higher - Utilities - Is there any common-area lighting?  

It's a very common mistake where an investor sold and bought properties and then when it's tax time they find out they didn't do the right process to actually qualify as a 1031 exchange.  

Not a common occurrence for sureI don't agree with the thought process that a RE broker would save you in this situation this is clearly title insurance and why you always want it..

This is quite common and you don't need an LLC for it. 

They sent a very professional slide pitch deck that showed all of their justifications around that specific market, e.g. employment market, housing shortage data, the new developments in the area, the air bnb data, etc. etc.They also stated the numbers were conservative (7 year to reach the target returns) and that likely it will be year 4-5.

It's great that you already have a home and potential ADU too since being self-employed in the arts can also have extra hurdles just getting approved for a loan. 

That is common from many lenders and it will also give you more time if need be if one of the other options does not work.