What are your biggest pain points with contractors and what would your suggestion be to eliminate that pain?

Needless to say insurance has been very annoying for me so I feel your pain. 

Extensive AirBNB experience tells me this is going to be a logistical pain in the neck, unless you happen to connect with the one guy who's got the opposite of your schedule. 

Everyone just has to remain true to their investment criteria.As painful as it sounds, the undisciplined actors are going to wash themselves out of an under-performing market, and the last thing you want is to go out with them.So how do you protect against that?

Real Estate transactions can be painfully slow and tricky. 

@Gary Nicholson I feel your pain, I would say if you are thinking of acquiring a property for investment rather than just a "free" place to live, look out of state.House hacking in CA specifically is for building equity in properties by the income you receive from renting out other units and using that to pay down a mortgage (increasing equity and hoping for appreciation). 

I wish I would have started out with Buildium because as I grow they have more features that I would really like, and switching is a pain.

The tenants can be a real pain and you have to stay on top of things, but the monthly rent check always came in on time from the section 8 department and they covered the security deposit also.

Matte doors would be a real pain to keep clean from hand prints and smudges.I've been using " light french grey" from sherwin in my flips and rentals

I hate banks too but at times, they are the cheapest means of OPM, albeit the biggest pain in the azz to deal with.