How do I know when paint is dry enough to pull the tape off?

Gail: Maybe this video will answer your questions

using painters tape diy

I painted stripes on my wall and I didn't remove the tape until the next day. Check with the tape manufacturer for their recommendations.

I pull it off while wet to make it easier.

Most advice is to pull it while the new paint is still wet. If you out so heavy a coat on that it is running into the tape, wait until that quits. If you wait until it is dry and have a lot of paint on the tape then it can peel off the paint. I personally have better luck with a slow steady hand and a good tapered brush, no tape.

Yes, best to always pull the tape when the paint is wet - this way you can also clean up an bleed-unders as well. Here is a project that I did for Hometalk Live and shows how I did the stripes - https://www.hometalk.com/diy/decorate/walls/create-an-accent-wall-using-decorative-rollers-29959955

Create an Accent Wall Using Decorative Rollers!!!