It is somewhat trial and error but a lot of it is based on recommendations. It took me 4-5 years before I found a handyman type that I trust to just take care

It is somewhat trial and error but a lot of it is based on recommendations. It took me 4-5 years before I found a handyman type that I trust to just take care of little things. But for other things I signed up with larger known brands. Like our AC maintenance contract is with one hour AC for all our units, this means they take care of preventative maintenance as well as fix things as needed at a reasonable rate. Plumbing I found through trial and error, and to be fair for any job where I see a bigger repair bill, e.g. > $500 I'll generally get quotes to keep everyone honest. There are exceptions of course, but when I start seeing bigger repairs being requested it sends up some red flags because we maintain everything really tightly. Our lawn service and our pest service are the same ones we have do all the units and our own home too. We found both of them through a referral and tried them at our home first. Then slowly gave them more.