At ten years into this come 2021, I see myself as a new investor still. Why is that? I came into this on the cusp of a TLD revolution, where just a couple years after I discovered domain names (cctlds, .com) all of a sudden there appeared a plethora of .awesomeness. I believed, and STILL do, that how amazing it was we could have an entire domain name BE the brand name right across the dot! Like, perfect fits!
So, over the years, I've bought like an enduser, not an informed investor. This has its downfalls. When you buy something because you like it, ie. as an enduser, you lose sight of the fact that many, many enduser sales were the one and only sale that may have ever been made on that name. Thus, me buying up new G's with just the lens of just an enduser, well guess what.. I was the only potential buyer for that domain!\
What I have learned is, there are a ton of variables and nuances outside of aesthetics. Just because a domain LOOKS good, doesn't mean it will sell. Just because a domain sells, doesn't always mean it has to look good. I have learned this from advice from the experienced hands on deck, given to countless other NPer's and myself. What I have learned is, you have to decide what you are in this for. Once you know that, you have to be willing to refine or even completely change your strategy in order to accomplish what it is you need.
It does help to be able to wear different lens and be able to focus on the "why". Why is those odd-looking names that don't make sense actually sell? Why is it there is such a demand for just one TLD, eg. .com? What I have learned is, rather than outright wearing blinders just because I don't like the aesthetics of something, it is better to try to understand it. You don't have to like or agree with something to understand it, and to give it fair chance.
Still I am learning, and still I truly appreciate the input and advice given day-in, day-out by those whom walked the path before us.