I used the lower of rent amounts for analysis. https://www.biggerpockets.com/analysis/rentals/ee5f6928-93ce... is link to the BP Calculation on it.

You can use the "bad roof" or other problem to negotiate a lower purchase price. 

In this case, your monthly payment with 20% down will have a good MARKET rate if your DTI works with a much lower month payment and no mortgage insurance(MI).

I know I already mentioned this, but @Mordy Chaimovitz...If you can get by with lower cash flow and invest for the long-term generational wealth (aka appreciation) in nice neighborhoods, that is the way to go, but it's tough to get by at times -- at least it is for me.Just know everyone's situation is different, and you should do what is best for your specific circumstances!

The numbers may be 30-40% lower than today's cost, but the process/approach to estimating may be good for you to review.

I tried calculating value based on NOI and cap rate (see below) but I'm new to this and the value seems to come out lower than I would expect.

page=LoadVirtualDoc&BookmarkID=6536) that capped annual increases to the Taxable Value of a property to the lower of 5% or Michigan's Cost of Living increase.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

The next gentrifying neighborhoods in Chicago are: Lower West Side; Humboldt Park, Gage Park, Ashburn, South deering, Hegewisch, Garfield Ridge & West Elsdon.  

There's a few different ways to focus on a lower rate such as with house hacking and making the investment your primary residence, requesting a significant closing credit from the sellers for standard rate buy-downs (which I've had great success with recently), or utilizing lenders who offer short term rate lowering solutions such as 2-1 rate buy downs (again, ideally paid for by the sellers).