Dont know your total situation , this idea may suck big time , BUT , if this prevents a major hit on your credit or a bankrupcy , you still have a roof over your head and it gives you time to regroup . 

think about your first 1 to 2 to 5 to 10 years of ownership of a property, and the difference between:-a 1-year old furnace under warranty, and a 35 year old furnace-a house with central air, and a house without-a house with a brand new roof, and a house with a 25 year old roof-a house with a knob and tube wiring, and a fully rewired housewhich is going to have more capex? 

This may include examples such as maintaining the landscape, a minor plumbing repair, doing shingle repair on a leaky roof or painting a few rooms between tenants.

But now on disclosure we will write something like "roof likely leaked" or something to that effect if we are replacing the roof and we are not sure if there were any active or past leaks.Originally posted by @Jonathan A.

My biggest CAPEX cost is either a roof or AC replacement.  

Outrageous considering we can re-roof and reside cabins by contractor without hitting a 10k deductible.

Then you can have the specialist sub pull permits for their work under their license, plumbing, electrical, roofing, etc.. 

Advantages of New ConstructionMinimal Maintenance: New construction means you won’t need to deal with a lot of the usual maintenance headaches—no leaky roofs, outdated wiring, or old plumbing to worry about.

Roof has been replaced in the past 5 years.

Exterior: Dayton Roof and Remodeling - Chuck Pest: Free Bee Pest Control - EricPlease let them know I recommended them!