They way it looks is for example the 1st comp would show poorly broken cracked driveway, I would high light that in RED and then in my property overview I would put in GREEN new driveway. another example is heating and cooling would put in RED the date of the systems ie:2008 12 years old and then put my report in GREEN 2020 new.

A few suggestions, make sure you have a strategy for splitting utilities between both units - with one heating and cooling system, one party may be cold while the other is warm.

No issues at all with me being away as long as you have the infrastructure in place of a handyman/plumber/heating person.

Will you have expenses like snow removal and heat if they're not there?

I once had someone go through the roll-off and haul 3 dead water heaters out that had been in the basement, and an ancient dead central heating unit.

At the same time each door is at a different location compared to a multi unit dwelling with duplicated services for heat, electrical services and so on. 

Property is a triplex:Apartment 1: owner-occupantApartment 2: tenant since 2 decade want to ask to move-out due to brother -in-law and mother-in-law arrive next year.Apartment 3: paying low monthly rent electricity, heating, water include 1BR for only $360/month

I am baffled that my "nice" home isn't valued as highly per foot as much as some transitional neighborhoods closer to the city where there are more crimes (look at a crime heat map), not close to shopping, the schools aren't as strong as the ones I'm zoned for, etc.

The fire was caused by an extension cord, coiled under a pile of clothes that was running a window air conditioner.The tenants have lived in the unit since 1994. 

Avoid anywhere with well water, septic, and oil heat.