, welcome to the MTC forum. Mostly what we talk about here is using the Make-The-Cut software to design and then cut out the designs we have made. Of course, there are lots more things to discuss, but that is the main purpose of the forum.
That said, what type of vinyl are you using? What kind of tool are you using for weeding? Are you using transfer tape to apply your cut design to the wood? What machine are you using to cut the vinyl? And are your cuts nice and clean with closed shapes that can be easily removed?
Assuming you are getting good cuts and have no problem removing a shape from the vinyl backing, it's possible you are using a kind of vinyl with a very aggressive adhesive, making it difficult to remove from the painted wood.
When you give us a few more details we'll likely have more suggestions for you.