Several recent upgrades: brand new driveway, couple year old roof (architectural shingles), New gutters, gutter filters, downspouts, drain tile for downspouts.  

The siding on the house was this terrible brown scabish siding (asphalt shingle looking), so that had to go as well.

Some places will not insure a home if,as an example, it has two layers of shingles on the roof.I would be up front with the lender and up front with your insurance agent BEFORE you even commit to a formal credit check on a loan to get answers.Fannie Mae also has some really strange rules you might have to abide by...talk with your lender.

A metal or flat roof is going to cost more than a truss roof with asphalt shingles. 

-New Roof ** (no leaks found from investigator, did of course suggest to replace since shingles were curving) // 7-8K-Front porch beam re-alignment * // 6-700 bucks-Landscaping (need to slope up sides so water doesn't flow directly into basement?

Tab vs architectural shingles, roofing paper vs full or partial ice/water shields, flashing, gutters, etc.Good luck.

You are roughly looking at $330/square for architectural shingles including tear off and haul away, drip edge, plumbing and exhaust vents and ventilation system. 

Do they still sell these weird shingles?

I see them around me , one side of the roof is black shingles the other side id white .

To me with the new truss system and roof "capping" the old system now the rubber is effectively a high mill vapor barrier. there is also a regular pitched shingled roof that the new roof tied into.