With the above being said, I am not an Oregon lawyer, but I did look up the Oregon Work Comp statute and the exact information you give, if the unlicensed handyman was injured at the home, he would have a great case to the work comp board and petition that he was your subject worker and thus is deserving of work comp benefits. 

I was stunned to find out he was reported on the media due to scams. https://abc11.com/unlicensed-c...

Painting will vary as well, a licensed painter will charge much more than an unlicensed one, best strategy is to ask actual contractors in your area.

And all my contractors love me😋 You and @Scott Williamson are hiring labor crews, handymen and unlicensed Contractors as @@Matthew Paul has mentioned.

I doubt there is a city in the USA that will let an unlicensed plumber touch it.

If you are unlicensed and just acting in a facilitating manner, not as a true property manager, all money passes directly from tenant to owner. 

Examples of 'wholesalers' who got caught (google Ohio Real Estate Commission Disciplinary Action Taken in 2021 and follow first link):[Name Withheld] (2021), unlicensed individual from Blanding, Utah was assessed a $1,500 fine for marketing a property for sale for others in the Dayton, Ohio area.

For example, if you were to use an unlicensed handyman that made a poor repair, if at some point in the future it is discovered due to a new issue, you could be responsible to tear it all out and correct the handyman's work.

@Tracy LeClairIf you put your LLC and you are not licensed as a property manager you also could put yourself in more legal trouble as the managers of the LLC operating an unlicensed pm firmIn these situations keep the LLC out and get a good umbrella policy

@Laura Heckenberg on small multi, a lot of the owners live close by and manage themselves, so a lot of time you won’t see management fees, and low maintenance expenses because they repair a lot themselves or use unlicensed contractors for repairs.