A tablespoon or two of skim milk a day won't hurt you. But how could you not prefer the taste of rich heavy cream in your coffee?!
Butternut squash is a healthy source of vitamin c, among other things, however, it is all dependent on your weight loss goals. Starchy vegetables, such as squash, carrots, parsnips, etc., should be avoided if you are attempting to lose weight. <50g of carb a day will yield weight loss. 50-100g will help you maintain your weight.
Pesto is fine as long as it is homemade. Otherwise be sure to check the ingredient label to make sure there are no funky ingredients in your store bought version. And I assume you aren't planning on pouring that sauce on any pasta...amirite?
Roasted almonds are actually considered to contain less levels of anti-nutrients, such as phytates, found in raw almonds. Eat away!