For the first pair of questions, we know how many things we are looking at, and are simply querying what the individual items are. For this reason, the question can, and must, reflect the number.
For the second pair of questions, we know that they are cups but not how many. The way we deal with this, when we don't know how many items, is to talk about it as the whole scene or ensemble, which is one item: this works regardless of whether there is one cup or two cups.
Is that one cup or two cups I see?
In this sentence, that is the scene or ensemble.
Some people confuse the terms collective noun with mass noun or uncountable noun. As a simple, relatable example, herd is a countable, collective noun. You can have one herd or multiple herds, even though a single herd is composed of multiple members.
Twenty cows are crossing the road.
A herd of cows is crossing the road.
Three herds of cows are crossing the road.
Likewise with staff. It is also a countable, collective noun. Each company has one staff, which is all of its employees as a group. Two separate companies have two separate staffs.
Individual:
Collective:
Uncountable:
Uncountable nouns can be used countably in informal language.
I'd like two waters please.
In formal language, they must be qualified by an amount.
I'd like two glasses of water please.
I'd like two drinks of water please.
I'd like some water please.
Note: there are many other meanings of waters that don't apply here. These usages are always plural and are rarely counted. e.g. the waters of Finland. We don't say two waters of Finland and the water of Finland has a different meaning.
Collective nouns are always countable, however, in British English, even in formal language, they may be used either as singular or plural without changing form (see elsewhere for the full details):
The staff is very happy (one staff)
The staff are very happy (the members of one staff)
The staffs are very happy (multiple staffs)
Best Answer
As long as the this is perceived as singular and the questions are perceived as plural there's no problem.
Consider the following example: