Factor 1: This is very, very common. People who make it into management often get there in part because they make quick decisions based on little information. You mention that you see it as your job to provide him with better information, but does he see it that way also? Unless you are getting in trouble for not giving him better advice, I would let this go. It is not your job to make good decisions for your boss or to worry about whether or not his decisions are good and take into account all the information out there.

That is something that has consistently gotten on my nerves throughout my whole working life and I have finally come to this conclusion. It is not my money, it is not my company, it is not my job to make those decisions.

#2: There are a few ways to handle this one.

If people are always asking for quotes on the same thing, you could make a questionnaire: How many people do you need to fit in your car? What color do you want? Will you drive it off road? Insist they fill it out and answer those questions before you give a number.

If that is not practical, phrase numbers in a very specific way. "A Toyota Corolla with four doors and standard tires costs $17k. It is too small for large families but gets the job done for a 1-2 person household."

Also, give out a range. "Cars costs can range from $4k to $100k depending on desired features, condition, and budget."

I find that most people are satisfied with a range, even if it is a big one. It's part of the education process. They may think they want the Hummer until they know how much it costs and what the mileage is.

Factor #3: Could you get your company to pay for PMP certification? I am not sure that it would help you with your current stress levels, but it's a great thing to get if you are in the field. There are some really useful techniques and concepts that may help you with your work. I also find that taking classes makes it easier for me to let go of some of the frustrations at work -- it gives me something else to think about.

It also gives you more options, which I find really helpful when I am extremely aggravated with a workplace. I've landed tons of interviews just because I have those three letters on my resume.