Has anyone tried American Modern? 

House ages can be all over the place, from historic mansions to newer modern homes.

They and another company with New York in the title have really struggled because they were too heavily invested in old-fashioned market investing.

Individual developers often borrow private money in the same fashion.  

=======Locate the septic feild(s)(s)(s).Have a scientific drinkability test on the tap water for any contaminates.Beware of big (and small) spiders in the basement.9 x 9 tiles are probably asbestos, same for the glue used to hold them down.Wiring and electrical panels may be at end of service life.Florescent lighting may be circa 1960 (I dream of Jeannie) lacking modern non-buzzing startups and be way to many for modern use (electrical hogs).Don't drink any of the water (or even get it splashed on you) without having it tested first.The building may have city water and well combination.Find all abandoned septic fields.Find out if the fire suppression equipment is up to spec with the local fire dept--inspections, types.Without a roof and with many broken out windows insurance may be hard to find.Paint--expect lead (the pealing type) of paint.Assume anything with capacitors-(HVAC, Florescent troffers, Kitchen electric motors, food service garbage disposals, etc.. )-the capacitors are bad--do not turn on until checked by a competent technician.Look for a basement.Look for fallout shelter(s)(s)(s) underground separate from the building (Duck and Cover Turtle era).Look for steam heat system and have it inspected for possible use or demolition.Look for abandoned wells, that may have dried up or were too contaminated to continue use.A phase 1 enviro would have been a good CYA move--you can bet any buyer from you will get one...Pay to have a written professional inspection done of the building to get a consolidated look at the things you will be facing.

Seems that banks do this in some fashion.

Well you cant do that.. you can be an investor which means you close and then resell but you cant market what you don't own .. in any form or fashion.. they were also investigating a RE broker who has made a career of listing certain wholesalers deals before the wholesaler close thereby aiding in a double close.. which they think violates the rules. 

People need to work to really be fulfilled, but things like the FIRE movement, Tim Ferriss, the drudgery of modern corporatism, etc has kind of made it seem that work is just a drag that should be avoided unless absolutely needed.

Often, you will need to dig deeper to get at the facts.I used to do my screening the "old fashioned" way.

I'm looking for my #2 house hack in a similar fashion but instead of managing 5 more tenants, I'm looking into doing section 8 where I can reduce work load with managing only one lease for a family.