It would be nice to exhaustively explore a tech before using it, but that's often simply not feasible due to lack of resources.

I suppose it depends on what you consider "significant" to mean. I have found close to 100% correlation between new technologies where I can understand the basic use cases and structure within a few hours and be moderately productive within at most a few days, and new technologies that have proven to be worth the effort in the long term when I've tried them. I can't immediately think of any exception to that rule within the field of front-end web tools I've tried so far.

I mean, that really ought to answer your question, but to be concrete: Never bet anything but maybe your startup on a tech that you can't find anybody else your size trying out. Try searching "$TECH sucks" and similar queries on the Internet. If you can't find anything, that's not a sign the tech is too awesome to have flaws... it's a sign nobody's using it! Of course, you need to learn how to balance the hype vs. the "sucks" options. The question is not whether somebody has something bad to say, the question is what bad things they say. Are they clearly using it wrong? Are they clearly using it in a use case the software doesn't even claim to support? Or... are they using it in exactly your use case in exactly the way you wanted to use it and encountered fundamental problems?

Even once you think you've settled on a choice, what other choices are there? The existence of a "good" choice does not preclude better choices.

If you do do a test deployment, don't fall into the trap of deploying at a radically smaller size than you need. If you're going to need the tech to work in clustered mode, for instance, don't deploy it to a single server and deploy three records to it. Deploy it in a cluster mode and load it up with 10-100x times the data you think it's going to have. You can't practically test the complexity of the app you wan to write without actually writing it, but you usually can test the size. Test your most complicated case; if you've got a web app and you want a framework to help you out, don't make the simple "user prefs" page, as soon as you can start working on the most complicated page in the site, which is probably the one that's the payload. Easy things being easy isn't an interesting test; check the hard things.

Find someone with a experience-hardened intuition to do this with you. Realize that any tiny issue you experience and can't get through now will become a large issue later. Realize that you generally always end up with some of those issues anyhow, so it's a question of picking which you go with. Don't underestimate the established choices. They're big for a reason, especially if they've been around for years. The new hotness will play up the old guard's flaws while minimizing their own. You can make anything look good by only considering the positives, you can make anything look bad by only considering the negatives. Always look at both for all options. Get that experienced person to help you through it.

For whatever task it is you are looking to do, figure out which problems you are most likely to have, and prioritize your analysis to focus on those. Do you know you need total CP consistency? Then you can quickly eliminate entire choices by whether they even claim it, and further eliminate more by checking whether they actually maintain it in the field on their user fora. Do you have price constraints? Bam, entire choices knocked out. I've never personally been in the situation where I got to the point where I needed to start kicking tires and I had a dozen equally-good choices; there was always a clear hierarchy.

And, in the end, do consider the joy-of-use of a tech... just don't make it your only consideration. An fun-to-use tech that completely fails to solve your problems rapidly becomes a nightmare-to-use tech anyhow. Ask around you about framework regret; anybody with a few years in should have at least one story of when they expected something to be awesome and it wasn't.

Even putting a week into something as important as "what database will we choose" can pay off huge, easily being the difference between project success or failure. You don't necessarily need to work everything out for months.

That's great advice. It's what I do. Helps find the trouble spots before I run into them.

It isn't just a web thing, but it is way worse in the web world. How many of the cases you described were for web shops?

If you're going to apply that standard, since to a first approximation everything is hooked up to the web, everything is web. In that case, it does no good to claim that "web people" are particularly prone to anything when "web people" are to a first approximation everybody.