The long "runner" beneath the topmost spot indicates that the paint adjacent (or maybe a little under) the tape hadn't dried thoroughly when you pulled the tape off, and created a "string" of paint that then adhered to the trim.  Using an old or dirty roll of tape means that the edge is dried out and doesn't seal as well no matter how carefully you press it down; so a combination of OOPSes probably happened to you.

To recover, get some GOOF OFF! and use it on a Q-tip to remove the mess. GOOF OFF is a nasty chemical, set up a fan to minimize inhalation and try not to get it on your skin.

What I do, however, is use a long, thin, plastic straightedge that I hold up against the corner, overlapping the trim or ceiling or whatever I don't want to paint, and paint along it using a foam brush (think of it as stenciling and pounce lightly).  Pull the straightedge away from the trim almost parallel to the PAINTED wall to prevent any paint strings getting on the unpainted area and wipe it between uses with a clean paper towel so that no paint is on the edge or back of the straightedge.  Then I paint with a brush to get about 4 inches of "border" and fill in with either a brush or roller.

Home Depot and Lowes both carry the painter's straightedge last time I looked. 

Paint bleed happens when you're not careful to press the edge of the tape into a corner, and then leave it on to dry.

The best way to avoid it is to glide your finger firmly against the edge of the tape to create a solid bond. When you're done painting, remove the tape while the paint is wet, pulling it away from the fresh coat so it doesn't smudge.

Good luck!