I think I understand better. The first thing I would say is you need to find a scope that can track (when you dial 8.3 mrad is it actually 8.3 or is it more like 8.2 or 8.4 or worse?), and keep on tracking, if your scopes internals have too much error throughout the elevation range then you'll start getting misses at distance that you think is the fault of something else. The good news is that most scopes in the $800 price point and above have a really good "track" record (and those that don't usually blow up pretty quick on the forums), but you should be checking your scopes ability either through a box test or tall target test. Outside of that, it really comes down to personal preference with regard to optical quality and what is acceptable whether you're a newb or a pro. I do not think skill level has as much to do with price point especially as the cheap(er) Chinese scopes have proven to be better and better over the years, and even the best of the best scopes at the upper echelon of price have had failure, so if a newb wants to buy a Tangent or ZCO or if a pro wants to put on a DNT or Athlon I don't think there's much to say about that.
I get quite a few PM's asking for which scope I think they should buy and my usual answer is: I have no idea, because I don't think there is any one scope for any particular shooter, so what I usually ask in return is what is the type of shooting you intend to do (near, far, hunting, comps, paper, steel, etc)? Are there any must haves you need in the scope, e.g. it must be FFP, it must have a tree reticle, it must be good in low light, it must be under 30oz. Things like that. From there I will ask them what their budget is and then I can start giving some general guidelines. I do not like just telling someone "get the brand X model XX" scope, but give them things to think about to help them make the decision.
The whole "buy once cry once" I think is a misnomer in that this rarely actually happens. People tend to think, "if I save up for that expensive scope I'll never want anything else" and then they buy that expensive scope and realize maybe the reticle is not quite to their liking or some other nuanced feature, or they start to think "maybe if I would have bought brand Y I might be even happier". If you can truly buy once and be happy in this game then kudos to you, you are able to do what few guys are able to do. What I hope to do in my reviews like this one here is give you an idea of how the scopes compared to one another in my testing, keep in mind this doesn't mean my results are the end all be all because there are many factors that could lean you in a different direction.
If you ask me if you should buy the Steiner T6Xi 3-18x56 or the ATACR 4-16x42 for example, I would have a whole bunch of questions for you and depending on your answers I might steer you in the direction of one over the other. For example, if you told me that low light capability is more important to you than weight then I would say you've already answered your own question. When we typically see these types of threads start up I always reach for the popcorn because I know there's going to be a plethora of different answers and half the responders will tell you brand X and the other half will tell you brand Y. I try to stay away from the brand wars, it is an argument that will never be resolved and will likely be dominated by faneurisms (what happens when a fan boy has an aneurism when someone throws their brand under the buss) on both sides.
Okay, back to skills right, that was your question. If someone is just starting out in the sport I have no issue whatsoever if they want to start out with a "cheap" scope, but I would also say this, with cheap scopes usually comes some heartache so make sure you buy from a reputable manufacturer with a good track record and also a good warranty. Over the years I have avoided Chinese scopes like the plague, five years ago and prior pretty much any scope out of China would crap its pants after a few weeks to a few months of use, is that really worth the hassle, but seasons change and we are seeing a new season for Chinese optics because reputable manufacturers are putting better QC in place. I honestly think that a good Chinese optics manufacturer can likely build an outstanding scope that performs well optically and mechanically with the right QC in place. Now, arguments about whether or not your scope was built by slave labor (although I feel this is somewhat disingenuous because couldn't the same argument be made about your phone, or the motherboard in your computer or... and the list goes on, and on and on) or you don't want to support the CCP, I get that, but that's another argument entirely.
To be honest, I'm not entirely certain I've even answered your question, but you bring up some good points that cause me to think if I could do something better or differently in my reviews that could help an even broader audience.