For videos, I don't think that's a big deal. I agree that if you give your regulars a heads-up about the upcoming price increase, it'll be fine. If they haven't bought them yet and they don't buy them after you tell them, they probably weren't going to be buying videos anyway.
As for regular tip menu items, it would depend on what items on your menu you plan to increase and by how much. If you take a page from retail sales, you want to make it seem like the customer is getting a better deal, while at the same time increasing your revenue. For example, if you had before 1x Spank for 10t, make the new price 3x Spanks @ 25t. What you want to try to avoid as best as you can is a straight up increase for the same thing (e.g. song request @ 100t > 150t). If you can, come up with new menu items to mix it up, and avoid those 1-to-1 comparisons. But then next year, you can come back to this same menu with increased prices after everyone has forgotten what it used to cost.
In the end, your regulars should understand that it's a business and things can't stay the same forever.