Is the simplest explanation always the better one? Not necessarily but as the phrase goes "all other things being equal" then I'd say it's a good start. The key is all other things being equal. I honestly think this works best when it comes to things like conspiracy theories or motivations. Again, I totally get the opposite side but I consider this more as guidelines, not hard and fast.
The simplest explanation isn't the less complex in terms of the difficulty to understand it, but the simplest explanation is the one that has the less assumptions. Lets say that gravity may occur due to the complex laws of physics that try to explain it, or from a demon that is pulling us down. The idea of the demon may seem to be the simplest one, as it doesn't have many complex calculations, but in order to explain that theory we should explain were did the demon come from, how can we not see it, why is he pulling us down, and many other assumptions and questions that would be impossible to answer. The fact that the laws of physics carry the less assumptions makes them the simplest solutions to a problem.
I believe the goal of explaining anything is to simplify it as much as possible in order to assist understanding without watering it down to the the point that it becomes vague. The depends part is that simple is subjective.
An explanation of how algebra works may be simple to someone with an interest in mathematics or someone studying for a masters degree but completely alien to anyone else who has no interest or exposure.
Ockham's Razor may be good for science, but bad for philosophy and religion. That type of reductionism can be problematic; it excludes too much data. Not all data is scientific. If you say we should only believe what the scientific method can prove, you're contradicting yourself, for the principle itself cannot be proven by the scientific method.
Everyone has a different 'simplest explanation' they think is most easy. Simple is usually easy to understand, right? But Easy isn't always the best. What if someone understands a pretty complicated explanation that seems 'simple' for them because they might be more experienced?
Simple is simple. Simple may explain some things that make it easy to understand. But if you already understand something, how are you challenging yourself by reading 2nd grade book levels just so you can understand them. If I only read books with 2nd grade book levels, I'll never learn to read harder book levels. Yes it's easy to understand, but you don't learn how to understand hard things if you don't try and always go for that easy. Yes it makes learning easy, I do agree on that.
The simplest explanation in the context of Ockam's razor is adding things you really have no reason to add to the explanation. It is about needlessly complicating the matter, or choosing answers that beg more questions than they answer.
Commonly used these days in talking about god claims, people look at the beginning of the universe. They leverage god as an explanation, when it simply complicates the question. If the universe needs a creator, why doesn't go need a creator? It is invention of an infinitely complicated thing to solve a problem we don't have the information to solve yet, with no particular reason to add that variable other than people wanting an answer.