If you have a Black and Decker circular saw that you paid $39 for and it does everything you need it to do, there is almost no reason to buy a $300 Dewalt.
If your needs are more specialized, and you want a little more power and a lot higher quality, then you might spring for the far more expensive tool.
I moved up the the R9 from a Keltec P32 because I wanted both more power and more accuracy, and I was willing to pay four times the price for it. Is it 4 times as powerful? No. 4 times more accurate? No. And since my P32 was/is flawless so far, I can't say the R9 is more reliable, either.
And yet, yesterday I was looking at pocket knives on Ron Graham's forum that cost even more than a Kel-Tec, and there are knives out there that cost more than a R9. Are they worth it? Maybe to some, but I'm not ever likely to spend $250 on a pocket knife, unless I win the lottery, or have real reason to believe that I will have to defend my life with a knife in the immediate future. Neither of those situations is likely, so I'll stick with my little Chive and save my money for ammo.
No one else can tell you if a purchase is "worth it" to you. They can only tell you if it was "worth it" to them. You have to decide for yourself which you want more, your money or another really expensive gun.