Should we reconsider our attorney's recommendation and go for a single revocable trust or is there a more efficient way to handle this with separate individual trusts? 

I may be a little bit biased, but I believe Chicago is one of the best cities in the country to house hack.   

Reasons to sell the seller on the Owner financing might be, because you are going to do a substantial rehab to the property, or that the property doesn't have any buyers, and this is a way to sell the property.Seller Financing works a lot better when there is not a realtor to pay, where a realtor's commission could be 6%, which on a $300,000 Purchase would be $18,000.An additional option you might consider if you are looking at purchasing this property to do a flip, or fix and rent, is you could propose seeing if the seller would partner with you, and you would secure a Private Loan for 50% of the sales price, plus the rehab, and if there is enough upside equity, you would probably be able to do a cash out refinance and pay off the seller that way.

Hi All, Does anyone have suggestions as to the best Commercial Real Estate Investing Course(s)?

The zoning wouldn't come into play.So assuming this is dirt and to be developed, I agree with the poster who suggested that the highest and best use is likely a commercial oriented use.

Just seeing if anyone has another way to get in contact with him.

We do this type of analysis in Reno, but instead of going one property at a time, we do it for the entire market simultaneously, so our clients can see the best deals based on potential cash flow and compare them to others in the market. 

That’s a great approach—sometimes slow and steady is the best way to go, especially when it comes to managing costs and avoiding unnecessary debt.

I've managed to house hack my way to owning a fully paid-off 2-bedroom, 1-bath, 900-square-foot home valued at approximately $67,500.

Best,Callaway