There is a big distinction on the variety of restrictions you need to be aware of with ADUs in Chicago specifically.

Wanting to incentivize/help those of retirement age to sell who won't sell/downsize because their new smaller home would be at a higher interest rate. 

Property values continue to grow in value, and you can actually live off the rental income.I think it's best to hav all properties paid off by retirement age, since that's when you are going to rely on cash flow for your living expenses.

Second, the ownership of the relinquished property and the replacement property in the three (3) Private Letter Rulings involved two distinctly different taxpayers.

Amazing goals for such a young age.

On a side note, oddly, the tenant before her was also a single woman, around the same age, stayed in the apartment for 10 months, no communication or heads up, left around the same time of the year.

With that in mind, I’m considering purchasing four rental units over the next four years to build a stream of income that could help supplement my retirement by age 68.The challenge I’m facing is that the deals I’ve come across so far don’t make financial sense.

I will return to this situation in the end of this post, but first let me show you why the age of a person can be tricky when it comes to the IRS.

Age is relative. 

I think we will see more "adult" families living together...kids move back in or parents move in with kids.The traditional apartment model was based on 12month leases, but jobs are not always 12 months and people want flexible terms, so co-living often offers that.Seems like younger people between 20-30 and some other age groups don't want to get married and start that housing pathway our parents and grandparents took.