Toss together the bread cubes, 2 tablespoons of olive oil, a big pinch of salt and several grinds of black pepper. Spread onto a baking sheet and bake for about 10 minutes, tossing halfway through. Remove from oven and set aside.
Meanwhile, make the dressing: Add the flesh of the avocado, along with the next 5 ingredients to a blender or food processor and blend until smooth. Stream in the olive oil and add salt and pepper to taste. Dressing will be thick - you can add a couple of tablespoons of water to thin it out if you so desire. Pour dressing into a jar and set aside.
Slice the cherry tomatoes in half and place in the serving bowl. Toss with a pinch of salt and some black pepper.
Cook the bacon until crispy; drain the fat and add the hot bacon to the tomatoes.
Once the bacon has cooled slightly, add the bread cubes to the bowl and toss to combine, coating the bread with the juice of the tomatoes. Add the lettuce and serve immediately with the dressing.
Salad is best served immediately after assembling, though the dressing will keep in an airtight jar in the fridge for up to a week.
Notes
This dressing is definitely tangy from the red wine vinegar, which I personally love. If you would like it to be less tangy, you could certainly reduce the amount of vinegar and thin out the final dressing with a little bit of water, if desired.