I had my toolbox stolen a couple of years ago, and I'm slowly building up replacements. It was at the garage of townhouse I was renting, and unfortunately found that my renter's insurance(to my surprise) only covered $100 in "ordinary household tools" so pretty much the only thing they would replace was a couple of screwdrivers and a couple of hammers.
Even going the Harbor Freight route, I quit counting how much I spent on replacing things. I've still made a few overpriced parts store purchases too when I was in a pinch like for a really big 9/16" wrench or an oddball size(usually big) socket. Fortunately I didn't have any 3/4" stuff. I'm still upset, though, over all the USA Craftsman I lost, some of which my dad and grandfather had given me when I'd taken an interest in car work. There was also a complete set of Whitworth wrenches and sockets in there, and I've only replaced two of those.
With "standard size" sockets, it can be amazing just how many you end up with. At the time they were stolen, I had a good range of 1/4" SAE and metric, 3/8" SAE 12 point, 3/8" SAE 6 point, 3/8" SAE deepwell, and then metric and SAE standard depth in both 6 and 12 point 1/2". My 1/2" deepwells were all impact sockets to do double duty(even though I mostly used them with hand tools), although I also kept a couple of standard 13/16" deepwells for lugnut use. I didn't have a full set over 1", but for the MG had 1-1/8" for the hub nuts, 1 5/16" for the harmonic balancer, and 1 13/16" for the steering wheel.
It's been a slow journey to replace all of those. I have lucked into some USA Craftsman, although what I have is not as well kept as my old ones were. I've even stepped up to some used Snap-On for some specialty tools-Snap-On can be affordable bought second hand, but I have a hard time justifying off the truck prices for my use.
Still though too, nothing is quite the same as my favorite old Craftsman 3/8" ratchet with the knob to change directions. The flip lever is more convenient and the rubber grips can be more comfortable, but that old ratchet was mine.
The real loss, though, when things are stolen to me is the tools I've made/modified myself. I'm sure everyone has the cheap combination wrench they bent a certain way to reach one specific built, or that you've ground down to have the clearance you need for something or whatever. Even if you no longer have the vehicle that required that special tool, the stories and memories behind making it are still valuable.
With all of that said, I was so glad that my watchmaking tools weren't in that bunch. I don't know if I even COULD replace those if stolen. There's a lot tied up in those, not just in the cost but the dear friend who passed away a couple of years ago who owned most of them and virtually gave them to me(I paid him a 4 figure price for everything, but it was a pittance considering that just the lathe was worth half what I paid) but more importantly mentored me in how to use them. He bought few of those new in the first place, but many of them can trace back through several hands that have used them. I have tools that are 150 years old and no longer made. I can't imagine trying to replace my much-beloved Levin staking set(I have a half dozen staking sets, but none of them are as nice as that one and I don't know when I last saw one for sale) or even something like the old 2 oz. brass hammer that is used for a little of everything.
To a watchmaker, your tweezers are your hands, and one of the few things I've ever bought new was a set of Dumont #2 pattern Inox stainless tweezers. It's hard to say how many times I've sharpened and straightened them. If you saw them, you'd think they were a badly abused set of tweezers or maybe even a Dumont #2 pattern knock-off(since the tips are shorter and a bit stubbier than a new #2 pattern) but none the less years of use have molded them to MY hand and nothing else, not even one of the other #2 sets I have are the same. There's a rack on top of my bench that has carbon steel Dumont #3c, #4, and two #5s in it. I also have #6 and #7 close at hand, plus some other specialty ones. There are times where I need to use the others(the #4 and #5 are smaller than the #2, the #6 and #7 have curved tips, and the 3c is smaller and has a totally different profile than the others). I deal with having to demagnetize the carbon steel ones every time I use them since the smaller ones hold their points better than stainless, but that's another discussion.
Still, though, again I can't even imagine having to replace my watchmaking tools. The thought of having to locate the perfect set of jewel setting burnishers, for example, sends a shiver down my spine.