The land and asphalt all add up by adding 10 ft.

DO NOT USE A PRESSURE WASHER . the oil soaked into the asphalt , if you pressure wash it you will blow the oil soaked asphalt away , making a hole .Call a professional seal coat company . one that uses coal tar , or asphalt emulsion .

The exception had original cedar shakes and they just replaced them with architectural grade asphalt.

They hit the pavement while you are writing code and making the donuts.

To find a good multifamily that gets closer to the 1% you'll need to search off the MLS and have your own feet hit the pavement. 

It’s only been 60 days and I’ve gotten some “near nibbles” but I can’t tell if refining my tactics would work or if I just put my head down and keep pounding pavement.

I just hate doing asphalt roofs.

The photo might look ok, but a quick check on Google Earth showed neighboring properties with untended lawns, peeling paint, rusting trucks, and cracked pavement.

I'd call a few roofers in the area off of Craigslist and ask them, in general, what they'd charge per square for a basic, asphalt shingle roof.

@Michelle BrightThat "silver coating" is an aluminium pigmented asphalt which is rolled {painted} onto an modified bitumen roof.