How best to get estimates for painting trim on house?

To properly answer, I would need to see photos of all sides of the house. My suggestion to getting estimates is go to your local Sherwin Williams and ask for referrals. Check out each one with the licensing and Better Business Bureau. Get a copy of their insurance with your address on it. Make sure that they pay Workers Comp and have liability insurance.

Call different contractors and get them to bid on your job. Trim work is quite time consuming, especially if the existing paint is peeling and needs to be scraped. Try to get recommendations from neighbors. The cheapest price may not always give you the best job. Make sure the painter uses a good quality paint and takes the time to properly prepare the surface. Ask for references of jobs they have done so you can go buy and see how their work holds up. Fresh paint looks good, but if it is peeling off six months later, it means the painter didn't do it right.

Call several contractors to come look at the house and give you an estimate. Make sure you get the estimate in writing.

Then give the job to the one with the best estimate.

Also, I would ask for two or three references from people that have used that contractor.

this depends on the city you are in. if the contractor is busy or slow. you can get prices from high and low.

why don't you just have the exposed wood wrapped in metal and its for life and it would not cost that much more than a paint job?

Call a painter and ask. MOM