I'm not saying this deal isn't good, but I would assume there's old knob and tube electrical in the walls with dangerous splices that have happened over the years.

How do a I find a company that can coordinate local property management AND online listings/customer service demands via platforms like Air, VRBO, etc?

Are there any rules of thumb for analyzing an Air BnB?

Things like:Location (dist to the coast could be an issue, fire protection in that town, etc.)Updates to the systems (knob & tube wiring, Aluminum wiring, fuses, asbestos siding, roof over a certian # of yrs, etc.Tenants (do any have breeds of dogs that will be an issue, are students an issue, etc.)That info will help when evaluating properties.

I am in a similar situation, im active duty air force with 2 young kids and one on the way.

(in my opinion, this would not make sense). bc you could live in the home or Air b and b it or rent it out while you finish the ADU. 

As the temp decreases, the dew point rises (assuming moisture in the air is trapped in the house).

Will,I would pay attention to the electrical (knob & tube or aluminum), age of roof, asbestos, or tenants with aggressive dogs. 

New windows, New Central air & furnace, new water heater, New carpet in basement and upper bedrooms, 1st Floor Hardwood floors.

Things the agent will want to know:age of the systems (roof, heat, plumbing, electric)if older, is there any knob & tube or aluminum wiringcircuit breakers or fusesany underground tanksdo tenants have pets (if dogs, what breed)what alarms do you havepitched or flat roofany claim history (check with existing owner)