I always see advice about which software to use and there's always the advice that FreeTaxUSA is the best bang for your buck and does everything you need for when your taxes are "simple." I've used and thought it was great for years. But as my career has grown and no longer filed as a single I've begun to question when my taxes and earnings become "complicated" to the point where it is worthwhile to have a professional do my taxes. Are there general recommended bullet points or scenarios?