The property cash flows and I could definitely see each investor making at least $1000/mo with the most hands-off approach of renting to an operator and much more if a person ran it as STR or LTR and it is a great diversification play for me as Costa Rica should see much better appreciation than the Midwest, but if I were to cash out I could see five times the cash flow because of the power of leverage.But I think you hit the nail on the head in saying that it is a lifestyle type of investment.  

The rooms are unfurnished and the tenants are very low-maintenance (hardly know they are there). 2+Unit Buildings here and nearby currently sell for $1.5M on average.I bought the property 16 years ago, so my mortgage rate is very low (2.2%) Even though the property is cashflow positive, my bigger play is the average 5% yearly appreciation.I'm looking for others who are interested in house-hacking in this neighborhood. 

And the reason why your "tale of two halves" will play out as you described.Demand:  This has actually been high almost all along, but rent growth hasn't materialized in response due to high levels of new supply. 

Depending on what you want to do and what role you want to play, would depend on how you should go about it. =)

The problem comes into play when those milestones are not good indicators of one’s progress towards a goal.

In my free time, I like to play pickleball, bass guitar, and I write real estate based articles on LinkedIn.

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

Detroit is literally one of the, if not THE, best markets you could be playing in today.

Sometimes the best investments are the ones you wait for.Here’s the kicker: utilities and zoning can make or break these plays.

They are great as appreciation plays but that's not what most investors are looking for.C/C+ is where you're going to cash flow...