shareware, no problem. There are only five questions and the tag isn't needed on any of them. Plus it's hard to think of an on-topic use.
freeware, I'd say not so fast. It has some other connotations and uses that could legitimately be on topic (not that it has necessarily been used in those ways in the past). There are 150 questions to review to see if any of those are an on-topic use.
Suggestion: cull the [freeware] tags as a first step. Many serve no function for the question and are simply unnecessary. Some may be clearly off-topic. That will reduce the questions list to a more manageable number. Then we can review the remaining existing uses and have a meaningful discussion of the merits of the tag or the need for any replacement tags.
Regarding the off-topic questions, only a minority of the questions are closed or on hold. This suggests that there are some on-topic uses, perhaps needing a better tag. Tag deletion for off-topic use, and closure for the same reason should go hand-in-hand. We should review the questions and flag those that are off-topic. When (and if), they are put on hold/closed, there is no longer a question about tag removal for those questions.
A few considerations:
I'll preface this by saying the following considerations may not justify keeping the [freeware] tag, or they may suggest using a better tag in some cases. The point is only the need to identify the facts and issues, and have the discussion before we arbitrarily delete all of the [freeware] tags.
Freeware is often used to mean open-source, and people don't use a thesaurus to pick tags. Keeping it, with a wiki summary that points relevant questions to the right tag, could be useful.
We ask posters to narrow their requirements as much as possible. A common requirement is that any solution must be free. A [freeware] tag does that.
"Freeware" is often used to refer to the ubiquitous free drivers and utilities that many people consider essentially an expansion of the OS bundle. We often treat those differently on SU from applications, particularly if it involves solving a specific problem rather than engaging in a general activity. There is also a difference between selecting the right tool from what is already there (or likely to be there for many people, or "should" be there), and shopping for something new. "Freeware" is a poor word choice for this and I'd have to think about what might be better; or perhaps no tag is needed for this.
Tags can serve a secondary purpose, to assist with screening and housekeeping. People are going to ask their questions. We might as well make it easy to spot the off-topic ones. A wiki excerpt that warns that the question is probably off topic, may deter a few bad questions. The tag can also serve as a magnet for scrutiny, making it easier to spot likely off-topic questions.
The existing questions may include some other uses that warrant a tag; if not [freeware] than something more specific.