I really hate the city because of taxes and water bills but the charming neighborhoods with a strong sense of community seem to be Lauraville, Beverly, Hamilton and Franklintown.

It makes sense to me but I foresee that to be a contentious point, even more if they end up not getting the rental.Thank you in advance!

Here are a few stats which should raise an eyebrow about Detroit $1 billion invested in more than 4,600 units of affordable housing over the past five years Job growth with more than 25,000 more Detroiters employed since 2014 A return to investment grade bond status for the first time since 2009Reductions in crime beating national trends, including the fewest homicides in 57 years Successfully hosting the largest ever NFL Draft at 775,000 people over three days In terms of starting out in Real Estate it also makes sense to invest in Detroit considering that the entry costs are low and if you plan to buy and hold, Section 8 makes for a great partner to insure steady rent payments.

If they are good, they don't have a problem finding work so doing your project at a deep discount makes no sense for them. 

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.

If you are using it to buy a turnkey property which needs to produce cash flow to be considered a viable deal how does buying turnkey(Little to no cash flow) combined with HML(High interest only debt) make alot of sense financially? 

A few more "common sense" steps would be to mark depth, post "at your own risk" signs, put "at your own risk" in listing/guest agreements. 

Once you find a good property and all the numbers make sense - pull the trigger.

You can determine if the cost segregation study makes sense by speaking with your accountant and many cost segregation professionals offer a free analysis.

Finally from a purely from a cash outlay prospective short term, you could rent a house with roommates and your payment would still probably be Lower than house hacking because rates are so high, over the long period 5-10 years obviously it would cheaper ti buy, hope that makes sense