It depends on many factors, but here, the 2 main ones apply imo
1: Was what you skipped really that unimportant? Can't you make a good scene out of it that shows something about your characters through those routine events? Then you shouldn't skip all of it, but maybe part of it
2: Does it cut into repetitive literary drudgery? (How many training montage episodes do you really need, Naruto?) If so, yes, some time skip after setting up the conditions, and maybe adding a payoff for it in a scene showing the progress. You don't need to see every swing of a sword on a mannequin, just the initial state and the result. The brain of the reader will do the rest. Well done, time skips are about correct framing.