We've done it both ways and in some cases with the non-registered contractor we came out well worse for the wear. My recommendation for your association is to stick with folks who are licensed and know what they are doing. Too much at stake for the association's officers to put themselves in harms way from claims by owners who could get angry if things go south. As far as your own stuff, be careful, there's some folks out there who have one goal i mind and that's to get in your pocketbook. Referrals are your best bet but even that is no guarantee.
You have to know them and know their work. I've only hired insured people in SC, but for my home in L.A. I've used uninsured guys for years, for huge jobs even, because I know them well and I know they do a great job. Hard to find those kinds though. I got lucky. There is a risk too that if they hurt themselves of the job you might be responsible.
If the project cost exceeds $1,000 or you're required to have a building permit, aren't you by AZ law required to use licensed contractors? I saw this definition of Handyman on a realtors website... I know many residents and contractors ignore the law, but you'll be SOL in getting any help from gov't agencies if things go badly with an unlicensed handyman. Even if you use a licensed contractor it's often hard to get help dealing with an under-performing contractor. I've seen plenty of shoddy work done by both handymen and licensed contractors -- and vice versa. Handymen aren't scofflaws -- licenses, insurance, and bonds cost far more than the typical handyman could ever afford. Whether handyman or contractor, your best bet is to check references and referrals, know your risks, make sure the contract is fully understood up front. Then decide.
