Kenny, it all depends....

Where are you in the USA?

Is the orchid pot bound?

Crawling insects? Most do not damage orchids.

What are your growing conditions?

And so on.

Hi, Arthur. I'm from the Philippines. It's getting warmer now. I can't upload the picture here I do not know why. It is still not pot bound. I will try to upload it again. Thank you. :)

I can't edit it now so I just made the picture my profile photo so that you can see.

It looks like it wouldn't hurt to give it some fresh media, I don't think it needs a bigger pot, just a refresh on the potting medium

I only repot newly purchased orchids if the pot size is too small/ too big, growing media/type of pot isn't ideal for my growing conditions or the growing media looks as if it has broken down. I sometimes will also take a new orchid out of it's pot just to elongate drainage holes,or make additional ones then I just plop it back into the same pot if all else is fine. Otherwise I leave it happily undisturbed.