TLDR; If the item isn't expensive enough to be willing to put in so many hours of your time and effort, then just always skip it. If the item wouldn't cause a major financial hardship for you to replace, skip it.
The big problem with small insurances is they are in most places poorly regulated, and even when operating legally are doing so in a way that is "technically legal" but actively deceptive using small print and ridiculously time-consuming claim processes. This is a polite way of saying they are, 95%+ of the time, a total rip-off.
One example is a major retailer here in the US sold (and maybe still sells) insurance on air beds. A friend of mine bought it, thinking it was only a few dollars and air beds go bad all the time, so maybe this would be a good bet?
Naturally the air bed started leaking, and my friend asked for my help because the process didn't seem to make any sense, so I called up the company. The operator read out the exact requirements on the insurance and had trouble not laughing while doing so, because it was one of the most rediculous things I ever heard. To be covered the bed would need to be losing air through no visible rip or tear, not through a seam, and not through the inlet valve assembly.
...so how, pray tell, could any item actually be covered? One that loses air through some form of internal teleportation? They gave a small nervous laugh and said that basically, yes, that does seem like how it would need to happen.
Similarly I worked for a company that sold electronic insurance, and I got to talk to customers that did and did not get the insurance on the items to work for them. I always asked how the process went, and not a single one said that they needed to make less than 4 phone calls, usually waiting for half an hour or more each time, they kept their original receipt and sometimes even cut out the UPC code from the box, usually sent a few emails back and forth as well, and it took around 2-3 weeks to get a gift card back. And that was when the company agreed to cover the item in full.
The trick is, most people don't have that kind of free time or sheer force of will to collect on what amounts to usually under $100 of 'insurance'. I know of one single major US electronics retailer that offers a 'protection plan' that is actually worth the money and not a hassle, out of the dozens of companies with similar claims.
Another common trick is to sell insurance on an item, but it turns out the fine print says it only kicks in after the manufacturer period expires (usually 1-3 years), even if the insurance you bought was supposed to protect from things the manufacturer wouldn't cover regardless.
There are an infinite variety of clever ways these companies have developed to take advantage of people, engaging in rent-seeking behavior to increase their profits while providing no useful service to most or all of the people who buy their goods.
Add this reality together with the uncertain risk that you would need it at all, and you'll find that the vast majority of the time these things end up as losing propositions.
If the item you are looking at is considerably expensive enough to be a real burden if it has a problem - like a car, house, etc. - then you'll need to try to do some research to see if that particular option you have seems to operate in a legitimate way. Then you'll need to read the fine print, keep up with all required paperwork and documentation kept in a safe place, and if it comes to time that you need it be prepared and diligent because you will usually spend many hours on the phone and by email/website/letter to get what is owed you.