I don't think it's a stupid question at all; in fact, I sort of "started over" in the past couple of weeks, rethinking my goals and strategies, and I ended up trading in quite a lot of stuff while getting some new tools.
It's important to be as clear as possible about your objectives; mine have become somewhat better defined to me over the past couple of months, and I finally found the courage and determination to go ahead and act upon my insights.
I think it's just possible to get there without some (or a lot) of experimentation, but I honestly think it's unlikely; I'm glad I usually hung on to the stuff I bought long enough to explore its possibilities and find out if it worked for me and what it could do for me. I found long ago that
is my preferred travel system - so I stuck with it but went ahead and culled the herd (three bodies out, one in; five lenses out, two in!). I found out that Nikon FF is the ecosphere I want to be in, so I sold all my APS-C stuff (two cameras, five lenses out) but kept the D750 and got the Z6 with a lens I didn't have before: a compact, yet compelling 24-70mm f4 so I could get full use of the FF sensor in a suitably compact package (as much as I still love the Olympus 12-40mm f/2.8, it can't do this, of course). I found out whatever everyone else is saying, I like Sony's mirrorless cameras just enough to find small kits bearable; I happen to love using the 55mm f/1.8 and quite like adapting lenses to the A7 II, so it's worth keeping that single body around. However, switching over to Sony completely is simply out of the question. I also found that whatever compact camera I carry, I want it to be responsive. That's why I may very well let go of the LX100 once it's back from sensor cleaning (yep, dust ...) - it's still one of my favourite cameras once it's switched on, but turning it on *and* off is a real nuisance (as is the fact that if you switch it on in your pocket by accident, it'll keep pushing out the lens, no matter what). So, if the coming Ricoh GR III does deliver the goods (i.e. beat its predecessors in crucial ways), I'll trade in the GR and LX100 to get a GR III (again, two out, one in); but only if that's the case - as I said, I really like the LX100 ... but sometimes, that's not the main point. As my EDC, it has already been replaced by the Canon G1X III. The LX100's lens and handling are special - but that's it for merits.
However, some cameras didn't even enter the equation: The Leica M10 is *the* camera for me if I want to enjoy photography to the fullest, full stop. I'm fully aware that should actually be a given if you buy into such an elusive system, but I still forced myself to honestly try it for real, so I used it as my main system while travelling, and it worked (oh boy, didn't it just - it was the most enjoyable shooting experience of my whole life). To mention to something completly different, the Panasonic FZ1000 is what it is: an amazingly cheap, yet amazingly versatile camera. It's the end of my wishes as far as bridge cameras are concerned - I don't use it too often, but when I pick it up, I know what I get, and even though I'm not that much of a fan of 1" sensors, I quite like the results. Lastly, the Canon G1X III is the best compact camera for me personally because it's just that: compact, responsive, sturdy, with the right set of features - just a no nonsense, no worries tool that shares none of the LX100's weaknesses (but also not all of its strengths - that's just how it is). In a world of imperfection, some things approach it from exactly the right angle - for your individual needs!
To sum up: Hang on to stuff that works until there's a worthy replacement - don't follow the hype (or if you do, do it with your eyes open - see my Sony adventure ...). Know what you need (or really want - which sometimes amounts to the same thing, especially if you're an enthusiast) and buy accordingly, don't follow every hunch. Wait, observe, decide. If you act, do it assertively - if you don't, you'll end up with a mess of half-baked systems or projects that don't amount to anything. Don't buy the best body and be stingy when it comes to lenses. Don't buy the best lenses and park them on a lesser body. Heck, don't buy the best body or the best lenses if you don't have the intention or the means to use them. Get what works for you - as specifically as possible. Don't let others take your decisions for you. In short, it's key to be honest with yourself. If you are, it'll work out. If you aren't, you'll lose out.
It took me a long time to take the right steps, but I'm pretty confident I'm on my way now. And interestingly, that means my inventory is shrinking for the first time in years.
M.