Barring economic anomalies or World Wars, this has happened like clockwork for the past two centuries:So theoretically we have ~6.5 years before the next peak in land value, which would be 2023-2024.

The Bay Area is such a real estate anomaly that is much different from Ohio.  

So if you find a good enough deal then you should be able to BRRRR your way through a few 2-4 unit homes, living in each for whatever the required time is for the minimum down payment and getting them cheap enough that you can get all your cash back out when you refi.Regarding cash flow, I also live in an expensive market (Hawaii, although nothing like NYC of course) where most condos start around 300-400k but I was able to find an anomaly building that is not pretty, it’s mostly section 8, and units sell for 100-130k and rent for 1600-1700.

Is Chase using higher prices to justify larger mortgages or is it just an anomaly of how they are estimating value in one neighborhood?

Maybe I'm some odd anomaly that you can't predict.  

--=================================================================ALBANY PARK : 4.88ASHBURN : 5.98AUBURN GRESHAM : 7.03AUSTIN : 6.03AVONDALE : 4.32BELMONT CRAGIN : 4.96BEVERLY : 4.39BRIDGEPORT : 4.22BRIGHTON PARK : 5.96CHATHAM : 6.61CHICAGO LAWN : 6.5CLEARING : 5.01DOUGLAS : 4.48DUNNING : 4.17EAST GARFIELD PARK : 5.72EAST SIDE : 5.38EDGEWATER : 4.09EDISON PARK : 4.12ENGLEWOOD : 8.98FOREST GLEN : 3.85GAGE PARK : 6.09GARFIELD RIDGE : 4.43GRAND BOULEVARD : 4.81GREATER GRAND CROSSING : 5.92HERMOSA : 4.54HUMBOLDT PARK : 5.47IRVING PARK : 4.12JEFFERSON PARK : 4.23KENWOOD : 4.44LAKE VIEW : 4.15LINCOLN PARK : 4.27LINCOLN SQUARE : 4.08LOGAN SQUARE : 4.19LOWER WEST SIDE : 4.45MCKINLEY PARK : 4.44MORGAN PARK : 5.94NEAR NORTH SIDE : 4.37NEAR WEST SIDE : 4.64NEW CITY : 6.93NORTH CENTER : 4.28NORTH LAWNDALE : 6.52NORTH PARK : 5.15NORWOOD PARK : 4.59O’HARE : 3.55PORTAGE PARK : 4.47PULLMAN : 7.38ROGERS PARK : 4.9ROSELAND : 7.62SOUTH CHICAGO : 8.51SOUTH DEERING : 16.58 * (only 1 property sold, so this could be an anomaly)SOUTH LAWNDALE : 5.65SOUTH SHORE : 5.88UPTOWN : 3.97WASHINGTON HEIGHTS : 5.89WASHINGTON PARK : 5.11WEST ENGLEWOOD : 8.09WEST GARFIELD PARK : 9.11WEST LAWN : 4.82WEST PULLMAN : 9.93WEST RIDGE : 4.38WEST TOWN : 4.08WOODLAWN : 6.02

Dig into the demographics of each zip code and look for anomalies.    

We're just going to need to be a bit more creative about the first couple of months so we don't bleed out too much money.Anyways, is this type of cost/process an anomaly, or have others come across something similar?

While I have not had to evict a tenant beyond filing initial paperwork, which is an anomaly consider the number of tenants I have had and an 8.22% eviction rate in my rentals' county, it is unfortunately a risk and cost of doing business.   

D.C. is a anomaly and can be very difficult to deal with from the tenant aspect.