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I think a lot of the equation boils down to how you're going to be able to use the car the majority of the time. If 95% of the driving you'll be doing in it is around town and on the highway, and your chances to really hit a fun road, etc. are going to be very limited, what's the point in paying more for something you can't use, both in up front cost and ongoing costs?
For me, a monster of a daily driver would be largely wasted. On a daily basis I pretty much just drive four-lane roads that are typically too crowded to do much of anything resembling fun and are too boring to make it worthwhile anyway, and stretches of highway that are also frequently fairly crowded, etc. On a typical day the most exciting thing I get to do it accelerate down an on-ramp, and even then 75% of the time there's some moron in front of me who wants to merge onto a highway at 45mph. I'd much rather put the money into a fun weekend car or two for when I can let it loose a little bit, and that can be tailored expressly for fun without any other considerations that a daily driver is necessarily going to entail.
Depending on what you get it may not end up being cheaper to acquire, but the upkeep costs will be less since you're driving it far fewer miles than you otherwise would, the fuel efficiency is less of a concern for the same reason, and depending on what car you're talking about insurance can be dramatically cheaper than a daily driver, especially if you can go with an enthusiast-focused insurer like Hagerty.
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