I wouldn't - that is nice-looking classic brick

No

I guess instantly devaluing a home is the plan becuase that is waht painting brick does .That huge out of scale chimney is ahuge issue IMO the rest of the house is quite nice

Not sure that would be the best direction for your home. Your home has exception brickwork that will be lost of you paint over the details.

Before I painted the brick I'd have it cleaned for sure to see what I was really dealing with. Then I'd consider painting the trim.

This colour of brick is not one I like at all. But I agree with cleaning it and seeing what you are working with. Also maybe adding colour in trim etc. The chimney is a lot. It is all I see when I look at the home.

No to painting the brick.

I would not paint the brick before a good cleaning as others have said. Painting the trim a darker color might be an option. I think a distracting visual to the home is the tall chimney but it’s hard to tell if it’s oversized or not from the photo. There is a rule fior chimneys called 3-2-10 that you should look up if you have a wood burning fireplace and maybe the chimney could be lowered. Good landscaping will also help.

I would not paint the brick, but I would paint all the trims a color.

I would never paint that brick, but, I would have it cleaned professionally. It will look brand new. Once its painted, you cant ever get that low maintenance brick back again.