Possible to Pickle Summer/Fall Ripe Tomatoes?

For a few years now, I have been buying the summer plum tomatoes at the farmers market. I'm too lazy to can, so I simply cut them into large pieces and shove them into freezer bags and freeze them. I don't bother to peel them. The peel sort of lifts off when they defrost. I either pull them out before I use them, but often I don't. I wonder if you would want to try this method and then make the compote fresh after they thaw. It won't be exactly the same as using fresh tomatoes, but I much prefer frozen over canned tomatoes. Worth a try. I also make a ton of Marcella's tomato sauce with fresh tomatoes and freeze it to use in the winter. It's a treat to pull that out in February.

Have you thought of possibly purchasing a few Kumatoes to get your fix? They're available now and sweeter than winter tomatoes. They might do in a pinch and tide you over until summer.

Your compote sounds delicious and, sadly, not something that could be safely preserved. The garlic and the olive oil are both difficult to can safely.
Do not despair. You could try freezing, although I think the texture will suffer.
Perhaps it's time to discover other types of condiments for the winter. I suggest giardiniera, chutney, chow chow and kraut as optional sandwich toppings.

You can pickle and preserve tomatoes but I don't think they will be like your fresh compote. My family makes a green tomato pickle but it is more like a chutney than what you are describing. I've made and canned salsas that are good but they have been cooked so the texture is different. Plain canned tomatoes are good for use in cooking but anytime you heat them the texture is going to change from crispish to soft.

I'm not a canner, so I can't give you canning advice. There are many good books on the topic (eg. McClellan, Mrs. Wheelbarrow) and some great recipes on this site. I do, however, make a number of relishes which I've frozen successfully (my favorite is Edna Lewis' green tomato chow chow). I also freeze homemade ketchup. I'm not sure if freezing would work for you here. Food for thought?