Bring a large pot of water to a simmer. Wash and core large tomatoes. Cut a small X through the skin on the bottom of each tomato. Plunge tomatoes into simmering water and allow to sit for 40-60 seconds (you will start to see the skins slough off). Remove tomatoes to a cold water bath to stop the cooking. Repeat with remaining tomatoes. Peel skins off tomatoes by grabbing the flaps of the cut X.
Cut large tomatoes in half horizontally and scoop out seeds. Place tomato halves, cut side up in a roasting pan.
Wash cherry tomatoes and cut in half. Squeeze or scoop out seeds and scatter with larger tomatoes, tucking some in along side the larger ones. Tomatoes should be tightly packed.
Trim herb stalks of any thick woody ends. Scatter herbs and garlic over tomatoes, pressing them down among the tomatoes.
Lightly crush peppercorns and along with the sugar and salt, sprinkle over tomatoes and herbs. Pour olive oil evenly over tomatoes and roast for 3 hours.
Pour boiling water into your sealable jars to help sterilize and warm them. Scoop hot tomatoes, along with herbs and garlic into jars. Top with remaining juice/oil. Screw on lids and allow to cool at room temperature, then refrigerate. If eating cold, allow to come to room temperature first, to allow olive oil to return to its original state.
-Seeding the cherry tomatoes is tedious, but only takes 10-12 minutes once you get going.