Wash and dry produce.

Quarter, core, and thinly slice pear. Halve, peel, and finely chop half the shallot (whole shallot for 4 servings). Quarter lemon.

Heat a drizzle of oil and 1 TBSP butter (2 TBSP for 4 servings) in a large pan over medium heat. Add pear, shallot, honey, juice from one lemon wedge, ½ tsp sugar (1 tsp for 4), and a pinch of salt. Cover and cook, stirring occasionally, until pear has softened, 5-7 minutes.

Turn off heat; transfer to a small bowl. Stir in juice from one lemon wedge. Wash out pan.

Heat pan used for pear over medium-high heat. Add bacon*; cook, turning occasionally and adjusting heat if browning too quickly, until crispy, 6-10 minutes. Turn off heat; transfer to a paper-towel-lined plate. Once cool enough to handle, roughly chop. Wipe out pan.

Evenly layer half the sourdough slices with gouda and as much pear as you like. Top with cheddar and remaining sourdough slices to form sandwiches.

Add bacon along with gouda, pear, and cheddar.

Melt 1 TBSP butter in pan used for pear over medium heat. Once hot, add sandwiches and push around in pan until butter has absorbed. (For 4 servings, work in batches or use a second pan, using 1 TBSP butter for each batch.) Cook until bread is golden brown and cheese is slightly melted, 4-6 minutes.

Add another 1 TBSP butter to pan, then flip sandwiches and push around again until butter has absorbed. Cook until bread is golden brown and cheese is fully melted, 4-6 minutes.

While sandwiches are toasting, in a large bowl, whisk together juice from one lemon wedge, 2 TBSP olive oil, ¼ tsp salt, and pepper. (For 4 servings, use juice from two wedges, 4 TBSP olive oil, and ½ tsp salt.)

Add arugula and pecans. Toss to thoroughly coat arugula.

Halve sandwiches on a diagonal. Divide sandwiches and salad between plates. Serve.