I want to go to places where the bathroom is in the basement and not think twice as to how I’m going to get there.Or use the bathrooms even in France that are holes in the ground with treads to squat on.. 

Simply cutting out bigger hole in the top.

House was never maintained or serviced and has holes all around the house as if they had punched the walls through out the years.

Could be a storm drainage on it the lot, easements, creek, river flood plain etc. 

Being an entrepreneur is primarily a role of knowing your strengths and recognizing your holes, then filling in people for those holes.Most all investment managers start with partnerships of two or three people that have complimentary skill sets, relationships, etc.  

Should I just patch the nail holes and patch paint them? 

All the sweat equity finally dug me out of the hole and I was ready for some rentals.

These included one of the outdoor lights not working, small common area repairs, tightening things, and a hole in a screen.

That will cover much of the issue and any remaining visible holes from the tack strip will be so close to the molding that it probably won't be noticeable from a standing position.

Each one wants to come out and look down into the hole and comment on what else you need to do.