My reason for creating this topic is two-fold, so I basically have two different, independent, “arguments”:
1 I’m dabbling with some changes to the marketplace, which might or might not ever see the light of day. As a result, I have to deal with this field. Since it’s “primary use” is for filtering add-ons, fixed options is the only thing that makes sense (as it already has in practice). I “dislike” that the options aren’t clearly defined in Core, because it means that when I want to do validation, I can’t use an “authoritative source” to validate against, but I must instead try to research what options are viable/in use (I even missed the schema) and then hard-code the validation based on that. It just feels wrong, it feels like making unmaintainable code.
2 As a user I have problems with the term “cloud”. Technically I agree with what you say, the term “cloud” is very vague and one can interpret it as meaning pretty much what one wants - so that it can end being “a synonym” to an online service/resource.
I have a very different association though, I see the term as a pure marketing term, with very little actual meaning. As such, I see those that use it as wanting to portray what they are doing in that marketing sense. The idea is something like “we’ll handle everything for you, and the future will be fantastic. Just lay everything in our hands, and don’t think about it”. Especially when it comes to “smart devices”, this is a very popular thing for the time being. Things that would have been accessible locally a few years ago, are often now locked in to a “cloud” where you have to give them all kind of information things they don’t need to provide the service (like name, e-mail, phone number, birth date etc). The “privacy policy” is often unreadable, and they change it often and with a very short notice. People will have to hire a lawyer to keep up with their “terms”. So, in reality, they do pretty much what they want with your information.
When I read “cloud” on an add-on, that is my association. I don’t think about it for another second, I reject it without even “investigating” what information is actually send - because this is a common arrangement these days, and I assume that’s what “cloud” means. But, this might just be me for all I know. I just assume that others see the world in a similar way.
If you dig into the technical details, there are all sort of gray areas. I would say that requiring personal or device identifiable information is a significant threshold though. Even though you can track IPs, query parameters and whatnot, linking that information to an individual so that it can be used for “profiling” of that individual isn’t neccesarily that easy. Even if they use cookies, I doubt the HTTP Java clients store these, and there’s not much to “fingerprint” like they do with browsers. They will probably be able to figure out that it’s a Java program using a certain HTTP client, from a given IP address and that’s it. If you’re worried about them logging your IP, you can use a VPN service. As soon as you need a login or must send e.g a device serial number, all that is out the window. They don’t have to “work” to make something out of very limited information, they can link it all directly to you. For me, that makes a big difference. The information can then easily be sold, or stolen, and used together with a lot of other data that is being gathered, to “profile” you. That’s what we shoud all, in my opinion, be worried about, and that’s why I personally would like there to be something that differentiates one from the other.
Regarding HA, I have just tried it once several years ago, so I know very little about it (the whole world of Python where “everything” is more or less broken at all times because of buggy code with no type safety written in a hurry wasn’t very appealing to me). When I look at what I think is their equivalen ot the “community marketplace”, I can’t really find anything like “connection type” there at least. The closest thing is their tags, there is a “cloud” tag, but I’m not sure you could really use it for that much useful. To find more information, I guess I’d have to install HA, but that’s a step further than I’m eager to go for this 
I know that currently, “connection type” isn’t supported by OH’s community marketplace either. But, what I’m working on would make it possible for add-ons to specify, which is why I think of the field/property as potentially becoming more relevant.