It's been posted here before about how difficult it is to find a good contractor in general (especially trees).

I'm thinking that the best practice to use when vetting any contractor is an absolute zero-tolerance policy. (This is assuming that the supply/demand issue is not totally against you.)

In summary: if a contractor is irritating, unresponsive, ignores your concerns, or acts stupid in any way, fuck 'em --- don't use them.

In other words:

If they don't respect your time - don't return calls or emails or texts, act stupid, forget the basic project you requested after you spoke with them, etc - block them.

If they insult you in any way for any reason - block them.

If they aren't responsive after giving reasonable leeway - block them.

If their bid is stupid expensive or their terms are stupid (want far more than 10% down to bind a contract, for instance) - get rid of them.

Those left are the ones you can deal with.

The guy I used last time did a good job but no longer carries worker's comp insurance. First question.....when someone does work on your property, do you ensure that they have worker's comp in addition to liability insurance?

YES

Liability insurance pays if they damage your premises or someone else's property (in tort law terms they are responsible regardless whether they take out insurance but most contractors can't afford to pay even a minor property claim.)

Workmen's comp is a standardized plan that pays for listed injuries in a specific way. JoFrance is not on the mark here - My understanding has ALWAYS been that if you hire someone to work on your property, YOU are responsible for their injuries. Yeah, you want to insist they carry workmen's comp. It's expensive for tree services (actually that is supposedly the most injury prone occupation.)

I called my homeowners and they said they would not cover if something were to happen and the company did not carry worker's comp.

Yeah, what I said is probably why they said that.

Out of four estimates I received, three contractors did NOT carry worker's comp. That was a bit surprising even though they were small time operations. I did find a guy that carried worker's comp and his estimate was lower than the others.

I've found loose correlation between professionalism and size of business.

When I went to pay the bill, he had some online payment thing setup. There was an option to select a "tip" (10%, 15%, 20%, other). I have never heard of tipping a contractor before. Since they were quite a bit lower than the other estimates, I did give them 10% since they were able to fit me in ahead of schedule. It's a bit weird to be tipping contractors though IMO. Never heard of that before. Have any of you heard of this or done this?

You tipped AFTER work was completed, right?

I'm seeing suggested tips popping up on carry out food receipts and even product type stores where I never saw them before.

My reaction is that it's fine and I would have done the same as you and yes, that is a new pattern.

Just a few things I thought I'd throw out there. The most interesting part is the career change from IT to arborist. Sometimes I think about switching to some type of blue collar trade like HVAC but am probably too old to make that move.

I should have seen the handwriting on the wall in ... 1991. I should have pursued a new degree then.