Honestly, there's no such thing as a bad time to start a Harry Potter marathon, but it's no fun to start the movies and not be able to finish all of them shortly thereafter. A singular movie of the series is not as satisfying than all eight movies. But there are perfect times to start a marathon. To watch all the Harry Potter movies, it would take roughly 20 hours, so you definitely need the time to finish all of them.
1. On a Rainy Day/Weekend
When you wake up in the morning and it's pouring outside, there's not much more you'd want to do than stay curled up in the blankets and watch movies. Unless you wake up at four AM, it's unlikely that you'd finish the movies before the following midnight. If you're a night owl and can watch movies from roughly 9 or 10 AM to about 5 or 6 AM the following morning. If you can't stay up that much, it would be best to watch the first four or five movies on one day and then the left over movies the following day.
2. During a stress-free week
If you have a week free of your busy schedule and can come home to relax after work or classes, you could stretch the marathon across a whole week, watching both parts of Harry Potter and the Deathly Hallows in one day. This would allow you to have a relaxing week watching the movies you enjoy the most. Honestly, this is one of the best options to watch all eight movies.
3. When you're sick
Feeling under the weather, sluggish, and overall cruddy, there's nothing like your favorite movies to cheer you up. Whether or not you watch the movies super seriously, switching them out back to back to finish them all before you have to head back to work or classes, watching these movies are bound to put a smile on your face despite the fact that you can't keep much food or water down.
4. With friends or family
If there's someone you share the love of Harry Potter with, then watching a marathon is a perfect way to spend some quality of time with them. While you both recite all the lines each character says (including their accents) and hum the background music, you'll share some magical moments that you'll remember forever. It's also a good way to share with a family member something that you might be passionate about, even if they don't particularly care for the movies. If they're willing to watch with you and allow you to show them how much these movies mean to you, then you'll both walk away from the quality time together feeling like you've shared something special.