I know that some flippers will pay the penalty rather than taxes when it sells... but it's racked up some pretty good taxes and penalties so far.

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.

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 . 

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.. 

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

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New construction means you won’t need to deal with a lot of the usual maintenance headaches—no leaky roofs, outdated wiring, or old plumbing to worry about.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