As others have indicated, there is a cornucopia of information and experience roaming these virtual halls.While most of the information has universal application, be aware that in areas of finance, regulation, and taxation much of what you find here will have a strong U.S.A. bias and, in many instances, things are done differently here in Canada.  

It all depends on how many workers are there, certainly 1 person cant consume $5,000/week when he is only painting, or it only takes 1 day for 2 persons to install a 4 appliances that values at $1,500 each.That is why the contractors are here because investors don't have the skills to operate renovation, if they did, why hire a contractor?

The Dept of Permits and Planning are currently hiring more employees to crack down on illegal rentals which is probably bat 90% of VRs on Oahu.

But I have to hire a good property management. 

I need someone to come out by Monday night at the latest because I'm in contract to buy the house and I need to get back to the seller"..Tony , when you say this to a contractor , its like saying  , Will you rush to come out and waste your time looking at a house I might  buy , and maybe I will hire you to do the work .

Depends on what rental property you buy.Depends on whether you self manage or hire a property manager.If its a SFH manager by a PM it could be totally hands off for you.

If one of my PMs goes bad, I fire them and hire another.

I own a property in Boston and wanted to know how landlords hire contractors for snow shovelling to comply with city ordinances.  

My background is in corporate finance and I moved to Washington 5 years ago from Hawaii after getting hired at a company here.

Traditionally I've been big into stocks and other more liquid assets, but a couple years ago I hired a guy who was a former house-flipper.