What decides the price
Three things, in this order. First, whether the reservoir is engineered or incidental: a designed sub-irrigation system with a float gauge and a separate granulate layer costs several times what a molded shelf above a puddle costs, and it is not a scam - it is the difference between a controlled water column and a wet bottom. Second, material: frost-resistant polypropylene that survives a winter outdoors is genuinely more expensive than indoor-only resin. Third, brand and looks, which is where the rest of the money goes.
A useful way to sort the market: if the listing tells you the reservoir capacity, the manufacturer thinks of it as an engineered system and prices it accordingly. If it does not, you are buying a nice-looking pot with a shelf in it, and you should pay a nice-looking-pot price.
The mistake buyers make
The mistake is buying a self-watering planter and then watering it from the top out of habit. A sub-irrigated planter is designed to be filled at the reservoir, and top-watering it defeats the air gap that keeps the roots from sitting in water. The result is the thing everybody is afraid of with these pots - root rot - and it is caused by the user, not the design. NC State Extension is direct about the mechanism: root rots are caused by fungal and fungus-like organisms that thrive in wet, poorly drained soil. A correctly used reservoir planter is not poorly drained. A double-watered one is.
The second most common mistake is skipping the initial soak. A brand-new planter with dry mix and a full reservoir does not wick, because capillary action needs a continuous column of moisture to start. Water thoroughly from the top once, let it drain, and only then start using the reservoir. After that, leave the top alone.
Where to start
If you have one plant on a desk you keep killing, start with the indoor roundup. If you are not convinced these are worth the money, the honest answer to that question is a better first read than any roundup. If you already own pots you like, a conversion insert is usually cheaper than replacing them. And if the whole thing worries you because you have heard these pots cause root rot, we address that directly rather than dodging it.