The answer is many times and never. Both at the same time.
It's a loaded question. A trick question, if you will.
I think that in budo, one will find themselves a beginner over and over again. Without having faux humility.
For example, just starting out in Aikido, I had trouble learning to roll. It took me awhile but at one point, I stopped being a beginner because I could roll from any direction. But, then (much, much later), I found that there are levels of rolling and I had to start the learning process over again. Not that I forgot the initial training at all, but the layer underneath would never have been found if not for that.
Who hasn't trained in something and later it just came out of the blue ... "Oh, that's what sensei meant!" And another level opened wide and you just felt like you had something brand new to work on -- at a beginner's level.
In training, you have to learn A before you get to B before you get to C. Well, sometimes around stage D, you realize that stage A had another level to it that you'd never have been able to work on if you hadn't progressed to D. Why do you think sometimes that the seniors always are quoted as saying they go back to the basics? It isn't because they've forgotten them. They've just opened up another level to them.
Do you think the higher level people just get what they are working on correct every time? They fail quite a bit, too. Just like us. But, they're working levels we haven't reached. And they're working them like we do -- try, fail, try, fail, try, succeed, try, fail, try, fail, etc, etc, etc.
It's why there's a love/hate relationship with Budo. There's always, always, always something new to learn but at the same time, you're always failing more than you're succeeding. In the overall scheme, you're going forward but it never seems all that quickly. Until you stop and realize that ten years have zipped by and you're ten years older. And the thoughts about not starting sooner creep in while you look ahead to all the massive amounts of progress you know you could make ... if you had the time. But, the funny thing is that no matter how young you start, it will always be like that. There is no end to Budo. There's only you and what you do today. Even if I was 89 and knew I'd die at 90, I'd still jump at a chance given to me to practice some martial arts. It isn't about gaining that judan or menkyo kaiden but about me and that day I'm training. Budo creeps into the bones and no amount of failure will dislodge it.