I think you know you're progressing.
You know the difference between your best stuff and the rest of the stuff. That's why you put your roman numerals sequence up front, and you're jump-cutting around some of the less interesting projects. But for the sake of your reel, you may want to consider cutting some of that older stuff even more. There's always this thing that happens when you make a big leap in your design skills, which is that you end up with some really great stuff and a whole backlog of work you're not that proud of anymore, and that mix makes for a reel that doesn't feel cohesive, and generally the old stuff drags down the new. Ideally you just keep working on new stuff until you have enough to pretty much fill a reel, but sometimes you need a reel for work. So what you kind of have to do is figure out how to spotlight the good stuff, and use the other crap as fodder and filler in a way that doesn't detract. And you have to somehow do that without making it look like you're spending too much time on certain projects. In other words, make the reel short, give the gold its spotlight, and cut the rest together in some way that we don't notice that it sucks. It's like taking a bunch of garbage and making an awesome collage out of it. We won't even notice the garbage in the face of the awesome new thing.