I know it is a pain but taping, especially the blue tape, is the way to go! Dh and I "teamed up" and set aside the time to tape and then paint. I think that is the most tedious part about painting is the prep work :)
Good Luck!

Never. You'd have to completely re-nail and fill nail holes and touch up the baseboards if you removed them along with any potential marks you'll get on them when removing. Tape works great if you have a hard time with the lines.

You never remove the baseboards for painting. If you were changing them or removing them to change carpet to hard flooring and then you'd install them and chalk before painting.

Sky

If you try to remove baseboard you will inadvertently ruin some of it and have to replace it. Get a good angled brush and a damp rag and get to painting.

I never have and I hate taping because it takes so long that by the time I am done I am too tired to paint. So, I generally will tape one day and paint the next.

I think you'll get a cleaner line if you do as Brutuses suggested. Don't tape if you can keep from it -- just use your angled brush to go right along the top of the baseboard, and quickly wipe away any drips or "oopsies."

I got my first painting experience last year when we finishsed our 1100 sf basement, but it was "virgin" territory--no baseboards, etc. Last month was my first excursion in painting an already "finished" room. I decided to tape off my moldings and tried a new tape I'd just read about--"Frog tape". I used it on the most visible moldings and the regular blue tape elsewhere (because Frog tape is a bit more expensive). I then cut-in without any worry and have a PERFECT line because the frog tape prevents any bleeding. To further protect my baseboards, I used brown paper (don't know what it's called--it's about 10" wide and comes in a long roll at Lowe's, etc.) along the baseboard, using the frog or blue tape to hold it in place. Place the tape at the top of the molding and score it to seal, but don't push the bottom of the tape down until you run the brown paper along the bottom of the baseboard, under the tape.

This work was more time-consuming and tiresome than the actual painting, but looks great in the end. I'm sure that with practice, I could probably cut-in the moldings just fine, but I need to get to that point first (I do great at the ceiling).

I cut in using an angled brush. Painters tape is a PITA imo. It does take practice to get a straight line, though, so a trick to stop bleeding when using painters tape is to put a light feather coat over the tape first, and let that dry, before you go with the heavier coat. That will seal it against bleeding.