First Car Search, Part IV: Is "old" school the way to go?

Right now, Lexus is in the same spot as Cadillac. They've seen their market grow older, and are looking to sell to younger buyers again. Though selling sixteen year-old me an old LS400 is probably not what they had in mind, it is the only way I can afford to contribute, as a $65,000 GS350 F-Sport is a little out of reach, and an LFA, well, you get the idea.

I know a lot of your probably aren't fans of the old, 90's LS (Lexus, not Lincoln). For many people, myself included, a fancy Toyota could never compete with the desirability of a European car. But right now, a German or British car may very well be the wrong choice for me. They are more expensive to work on the a Lexus, and pulling up in even an twenty year old one at my high school will likely get a few people to mutter about "spoiled rich kids" under their breath. The Lexus is too old man for people to remember that it isn't much different from an old S-Class, and I like that. I don't remember where I read this quote or who said it (it may very well have been right here on Jalopnik), but it talked about how ex-old people's cars are perfect for sixteen year olds. They fly under the radar, they are loaded with features, safety and non, they usually have powerful, reliable six or eight cylinder engines, and they have usually been dealer-maintained.

These are all the reasons I like the LS400. Big V8, RWD, safe, good-looking enough, and with more luxury features than I could ever need. But I still have some questions, even with a choice as seemingly safe as this.

A) Gas milage. I know this isn't a Civic, but it's also not a Suburban, and a 4.0 V8 is one of the smaller V8's you can buy in the US today. Could I get 18 city mpg out of this thing without driving it like Betty White?

B) I know these are cheaper to repair than a Mercedes or BMW, but with all those electronics, I still feel like there is a large potential for problems. Any repair horror stories for these, or are they as trouble free as legend says?

C)I know this isn't a high priority, but is it cool? I know that beige models are most common and driven by the elderly, but this one is black. Plus, they used one in The Sopranos, so it can't be completely dorky. Right?

Any other advice/comments would be greatly appreciated!