Upgrade from 458 to Aventador?

Not sure whether I should post this here or in the Ferrari section but I'll try here first.
I have a 458 that I think is an absolutely incredible machine. I love the looks especially from behind. I really enjoy driving it but the aventador is still the most amazing looking car on the road (not including hyper cars in this assessment - the laferrari alerta takes that one but alas it's out of my price range). The cars I'm looking at are the aventador coupe and roadsters. I prefer the roadster. Here are my concerns:
1) it's twice the price of my 458, am I getting twice the car?
2) the roadster is a relatively new car. I don't like losing too much money on my cars. I'm a businessman and I look for good deals in everything from cereal to homes so far that has meant buying and selling my exotics at pretty much break even. I got a 360 spider that I enjoyed a few years, then sold. Had a gallardo for 4 years, sold it for $5K less than I bought it for. Got my 458 at a great price and my loss will be minimal. I don't have the kind of money you'd need to not give a crap about losing $100K in a year or two. Everybody's different, so what are people thinking a 2014 roadster with less than 10K miles will be in 6-12 months? They are currently around $350-400K. According to my calculations, looking at depreciation history of exotics they tend to drop 35-40% in 6 years from release, and then flatten out or drop less than 2%/yr. It also doesn't seem like heavily optioned cars are rewarded in the aftermarket because of subjective taste or other factors unknown to me.
This calculation puts the aventador roadster fully depreciated in about 2019 at around $260-280K. I am ok taking a $30-50K hit but anything beyond that and it just doesn't make sense to me. Conversely I don't want to be an old man driving it. Trying to find that perfect timing to buy it. Any pointers?
3) people who have driven both the 458 and the aventador, what do you think makes it absolutely worth the upgrade? It isn't really much faster than the 458 and has a single clutch. Visibility is worse, tires are custom, it's less practical, less nimble and more maintenance (from what I hear). But wow it looks so good.
4) I don't like the huracan (it doesn't excite me at all) so please let's not get into that

Thanks for your input!

 

Haha I like that and can definitely attest to the level of attention you get in even the gallardo vs 458.

 

So far I've only been a passenger in one but will drive one soon. I was in a 2014 roadster. It felt faster than the 458 (it does have nearly 700hp, but then again so does the hellcat ) but I've found that sometimes being a passenger the car feels faster than when you're in control. Might have something to do with anticipation. The sound was brutal and amazing and it looks simply stunning. It's visceral. All about attention and drama. As I went and got lunch in my 458 today I realized that I probably could never have done that in the aventador. I've never had anyone stop and take pictures of my 458. I did all the time with the gallardo. To me it's a double edged sword. Being in the passenger seat of the aventador I realized it felt more rigid than the Ferrari, as if the suspension was stiffer. It also seemed more glued to the road, which is probably attributable to the AWD. The Ferrari just feels lighter and more nimble. Like Anunakki said, more toss able.

 

I think if the aventador and 458s had comparable performance, and comparable price, I'd get the roadster. What I like about the lambo is mostly the design and I already feel like the 458 is way faster than what's really necessary to have fun. For mountain roads the 360 is actually perfect in that it didn't accelerate so fast as to get you in trouble before the next apex. You could also throw out the tail quite easily without too much drama. I don't think I'd ever have as much fun in an aventador in the mountains, but it's unsurpassed as an attention grabbing cruiser. Ah, the dilemmas!

 

As with everything materialistic in life the novelty eventually wears off and you're left with something that starts to look like a bit of a mistake. I've had that happen with everything I've owned my entire life, with very few exceptions. Yes, the aventador looks great, and would be wonderful to own for a while, but it seems to be at a price point that only makes sense if you're sitting on so much money that you wouldn't care if the car lost all its value (or half, which it will). It's really a car for young people, bought mostly by older people. I can't quite decide whether it's a car for people who want to be seen, or people with a passion for marvels of engineering and design. I also think it's more of a status symbol for rich people to go with the trophy wife, the cartiers, designer handbags and vacation home in the hamptons. In that sense it is not for me. I just like it for its design and visceral driving experience, which means the price of admission may be a waste since the greatest selling point seems to be the status of it as a symbol of wealth. Maybe I'm wrong.

 

Thanks for your input so far. Lee, since you own both, which one would you say you reach for the keys for more often? And which one puts the biggest smile on your face? Do you find the extra money over the 458 worth it? How have you found the maintenance on the Ferrari vs lambo?

 

Wow, thanks so much for taking your time to write, Lee! I appreciate you sharing your experience. The 458 has indeed been perfect for me too save for a few minor issues mostly relating to voltage/battery. To me it's interesting that you have a Hellcat because that was going to be my argument against the aventador. "But the Lamborghini has 700 horses! So does the hellcat.". I think at the end of the day you're paying for a driveable jewel, a design that is extremely unique, a sound that is exotic and sophisticated and a badge that carries a certain status. What you get is all the above, along with the crowd to appreciate it wherever you go. I like your setup with the spreadsheet. I have 4 cars myself, and I try to rotate driving them but it's hard to keep track of. I might start doing the same. Thanks a lot for your comments.