I consider myself fortunate in that I haven't gotten swept up in the dream kit phenomenon. I am a big fan of intermediate kits.
I do understand very well why pursuing a "dream kit" is so attractive to so many drummers. I didn't go through this with drumming though, instead it was with photography.
In the beginning of my photography career, I did put a bit too much focus on acquiring really great gear. I did compensate somewhat for my lack of technique and overall creativity as a young photographer. Eventually I improved and nurtured my talent and became less concerned with having the latest and greatest gear.
Now that I'm older and have a little more money, I am still reluctant to drop big bucks on a fancy kit. I prefer to spend top dollar on cymbals and hardware and make my intermediate level drums work well for me.
I feel the same way about cars. I couldn't care less about driving a fancy car.. .. but I will only do synthetic oil changes.
You know what I mean?
Ya - I know exactly what you mean.
For me, I got swept up in creating sounds (and a little music too - ha ha) with synthesizers and computers.
The goal was to make music without the hassles of the 'playing drums with the band' thing that became unenjoyable for me.
Spent a ridiculous amount of money on the technical stuff, and still, every year, something newer with more capabilities seemed to come out.
I spent more time focusing on gear and manuals than on actual creative activities or practicing though.
Still going on without me of course, but I'm mostly outside now.
For drums, I'm really satisfied with my intermediate Stage Customs.
Still, 'under the influence' of this forum, I decided I had to have Maple Absolutes.
Didn't buy new, but came across a good deal on a used set and jumped on it.
I like them, and they sound and look good.
But truth be told, I don't play any differently on them than I do on my SC's.
And also truthful, the SC's sound just as good, but different in that they're birch opposed to maple.
The hardware is a lot better on the Absolutes though.
Like you, if I tally it up (shudder), I'm sure I've spent more on some quality cymbals than on intermediate drum sets since my re-entry.
Now I've got it stuck in my head to get back to my roots, and get some Ludwigs. (forum influence?)
I might, and I'm sure I'd enjoy having them, but I'm also sure I wouldn't play any differently on those either.
But ya - skills. I like to think I'm fairly competent on the drums, but there's always something new to learn,
some existing skill that can be improved, and something you stumble across that you didn't know of before that provides a new challenge.