Should I require handyman to have insurance?

[Dave Vona]

Hi, I'm just starting out and looking into doing some flips.  It's possible that some of the work can be performed by a less skilled contractor, such as the painting and maybe the drywall.  I was wondering if I should require the contractor to have both workman's comp and liability insurance.  This seems like it could be cost prohibitive for the smaller jobs and a handyman is unlikely to have this coverage.

[Samir Shahani]

@Dave Vona

My experience in life has suggested that whenever you take a shortcut (hiring an unqualified guy or trying to skip a step)  you end up paying more than the original price of doing it correctly.

I can paint (no pun intended!) a pretty bad picture for the scenario you describe:

Your non-malicious handiman hurts himself in on your property by mistake and sues you.  

You still have to get the work done & now you are dealing with a law suit!!