I'd buy an old luxury/classic car in mint condition and try to project an image somewhere between waspy old money and Don Draper.
Exactly. The Mercedes W123 or W124 is the perfect car for that situation: luxurious, built like a tank (and much cheaper to fix than newer Mercedes), available with a (relatively) frugal turbodiesel engine and sometimes even a manual transmission. What more could you want?
The key, of course, is it's gotta be mint -- it has to come across as "classic," not "old." Think like this.
have been reading this site for a couple months and registered to say that I am doing exactly this. The "Roger" clip is spot on, and is one I send to my friends on what seems like a frequent basis. they rarely listen.
I'm an attorney at a small/mid-size defense firm in Los Angeles. I have some private clients but mostly rely on the firm's large insurance defense business that keeps us profitable. Most of those clients are individual insureds whose policy is paying for me and thus have little say, if any, in their choice of attorney. I do have to care somewhat though, as I imagine someone telling their adjuster "that guy you hired showed up to inspect my property in a worn out 1992 Buick" might not go over that well.
I've avoided too much flash, but currently have a 2013 Audi A3 diesel on which I have a car loan that thankfully I will be getting rid of shortly when it is bought back by VW/Audi per the terms of the settlement of the diesel scandal lawsuits. Having recently stumbled on this site, I thought this was the perfect opportunity to use the surplus I'll be getting from the settlement to fund a cash purchase of a used car. But with my profession, and moreover, with my lifelong auto enthusiasm to satiate, a completely-utilitarian and sensible pick wasn't going to cut it. I settled on a W123 and I think it fits the needs perfectly. Oh also, I'm doing nearly all the work on it myself, which many in my profession probably couldn't say they're capable of. So that makes a difference too, since parts on a Honda would certainly be cheaper, but I can balance it out somewhat with labor, and the happiness I get from learning new skills whenever I get to repairs that I haven't tackled before.
I picked this 1984 300d up in July for $5k with 183k miles on it. It's not mint, but it's close enough that it functions as a totally serviceable daily driver and so far I've had nothing but compliments from the two clients I've visited driving it. The key was finding one with an interior in good shape, as there are countless examples on Craigslist for $3k or less with interiors that are complete disasters. I feel like I may have overpaid slightly, but after watching the LA market for W123s for about 2 years, it appeared that a decent interior meant a jump in the price bracket to the $5-10k range.
Once my Audi is gone, I plan to budget for repairs on the Merc but those numbers will be drastically reduced from what the car payment was on the Audi.
It was cheap to buy, is cheap to insure, gets decent enough mileage, and has world-renowned long-term endurance/reliability if properly maintained. Yet, if kept looking nice, this car will project "connoisseur" in a way that I think Roger would approve of, without the steep buy-in of the average connoisseur car.
This was right after I purchased it:
And this is after initial work (suspension, lighting, and bringing basic maintenance up to date).
Next is putting the alloy wheels it originally came with back on with a fresh set of tires now that I've completely redone the front suspension and put it into alignment (had to pretty much replace everything). I'm having the wheels powder coated which I think should really help project the clean/mint condition look along with the clean face the Euro headlights/turn signals give. There are so many of these running around LA with wheels covered in age and brake dust that clean ones should really make a difference. Some people like the hubcaps but they're not to my taste (and not what this one originally came with anyway).