There's no need to wonder, it's not unclear, nor is it a can of worms. It's spelled out in the regulations, has been posted here many times, and is easy to Google if you so desire.
In summary, it says you must be able to see the drone with no visual aid other than prescribed glasses well enough to determine it's attitude, orientation, and direction of movement at all times. This includes whether it is moving toward or away from you.
In practice, this amounts to 1000-2000ft depending on individual visual acuity. The limit of being able to discern attitude is far shorter than the limit at which one can say they see a spec in the sky.
The problem with VLOS is not a fuzzy definition, it's that people don't like it. Me among them. I break that rule all the time, mostly flying FPV without an observer. I have absolutely no concern the FAA is coming to my door, as there's no risk to anyone. Whenever there is, I have a VO.
Cameras on drones changed the situation w.r.t. VLOS, and the FAA is working on it. Vic posts about it now and then. More flexibility is coming, at a typical government glacial pace.
So, can you maintain VLOS as defined in the regs with a 5000ft AGL flight? No, you will not.