Here's a short tip that will save you about an hour of your valuable time. I remember making tomato soup for about 12 people and it required all the tomatoes at Whole Foods Market; imagine individually hand peeling those. While shopping at Whole Foods Market, I pictured myself slowly peeling each tomato with a paring knife and having tomato juice fly in all directions. This tip will save you from a tomato-juice-filled kitchen.
Before boiling the tomatoes, use a knife to make a wide ‘X’ mark at the bottom of each tomato (as seen in the picture). After boiling, a gap is created between the ‘X’ on the tomatoes. You'll be able to gently pull off the skin with no hassle. Give it a try!