If someone asks -
Do you think spending an upwards of 100 bucks would make sense?
I think that means spending 100 more than something. But since they've not specified compared to what. Please, help me with what that means.
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"Upwards of" (or less commonly "upward of") means "more than" or "in excess of."
Accordingly, spending "upwards of $100" does not mean spending "$100 more than" some unspecified amount, as you seem to suggest in your question. Rather, it simply means spending some amount that is more than $100.
In practice, most native speakers would assume that "upwards of $100" referred to an amount not vastly higher than $100. That is, I might say something cost "upward of $100" if it cost $110 or $125. I wouldn't be likely to say that if it cost $200. Likewise, I might say I had lived in New York for "upwards of ten years" if I had lived there for twelve or thirteen years, but probably not if I had lived there for eighteen years. (In that case, I'd be likelier to say "almost twenty years.")
Please note that "upwards" is not a noun and does not take an article. We say something cost "upwards of $100," not (as in your example) "an upwards of $100."
Finally, please note the distinction between "upwards of" and "up to." If I said I was willing to spend "up to $100" on something, it would mean I was willing to pay $100 or less, but not more.
The dictionary definition is "more than." Under that definition, "Upwards of $100" would mean some amount close to, but greater than $100.
However, I've used and heard this phrase many times and it pretty much indicates that the actual amount is an indeterminate amount less than the stated amount and we are rounding up. So it would be a synonym for "up to." I just polled several native English speaking friends and they all agreed that is generally is a synonym for "up to."
My gardner charges by the hour. Sometimes he only charges $80 to do my lawn, but it could be upwards of $100 if the grass is bad.
This means the amount he charges varies between $80 and $100. If he sometimes charges more than $100, you might hear
upwards of $100 or more.
Which means it's normally less than $100 but very occasionally can exceed that amount.
A dictionary pedant would say that this is a redundant phrase, but it's very common. In fact, it's common enough that it's the normal way to hear things. A usage "mistake" kind of stops being a mistake at some point when it is common enough. Even if it is a mistake on some level, you are likely to hear it used this way if you interact with native speakers, so be prepared.
It also might be a localized definition, as I am located in the US and Mr. Harvey is in the UK.