Without population growth, your rental income will lag behind inflation, requiring you to find additional sources of income.How long your rental income lasts depends on the job growth in the investment city.Non-government jobs are inherently temporary.

For the son to qualify for the $250k exclusion, I believe he would most likely need to meet the ownership and use test, meaning he needs to own and live in the home as his primary residence for at least two of the last five years before the sale.

Last time I did that, years ago, I got off the phone and figured it out myself. 

It may work in the long term but can be a painful process.i wish the OP the best and i believe he can benefit by recognizing the value in the various responses but seems unwilling.  

@Jacob Dalton - I have been a landlord in Chicago for 13 years and as an investor agent I have worked with 200+ investors on the north side of Chicago over the last 10 years. 

Flat Fee MLS Brokers for sellers have been around for a long time, but Flat Fee Broker/Agents for buyers with a cash credit/rebate of the buyer agent commission are quite new and just starting to get some market share.

Check out traceestate.com I have been using them and the sourcing company that they incorporated for the last few years.

In the last few years, they've made illegal:-Rent controls of any kind-Limiting of fees or screening charges-The ability of HOAs to regulate STRs or LTRs in their neighborhoodThat's just the start.

Last time I checked only people who have lost a home are those who do not pay.

Im waiting to hear back to go look at the last unit.