Not quite a "What car?" thread, more of a automotive philosophical decision.
My current stable consists of the BMW E30 race car, the '65 F100 tow vehicle, and a steel car trailer. The Bimmer is a great car, pretty well sorted and I race with a fantastic bunch of guys. Downsides of racing are eternal expenses (mostly tires, which are Toyos, and we're constantly complaining about them), and the high risk of it being written off in an instant likely through no fault of my own. I'd never give up tracking something, so even if I would quit W2W I'd still time trial it or something.
The F100 I've owned for something like 9 years. I like it. It's a great conversation piece in any paddock, does the job when it's infrequently called upon, cost me pocket lint to buy and maintain and looks good from 5 feet away. The original intent was to refurb it to a really nice driver but other projects always seem to get in the way. It's got some rust issues that should be dealt with that involve painting, so there's no inexpensive way to go about fixing it. As-is, and living in the garage, it can probably continue without really doing much for the forseeable future. I just have guilt about not fixing it up.
The recent sale of my Mini has generated some disposable car cash. I could do any number of things, but my current choices are the following:
Classic car: aside from the truck, there's always been a collector car in the garage. After playing with little sporty cars for years, I'm wanting to scratch the itch of an American classic, leaning heavily towards a Ford Falcon. I've never had a V8 in a car, so would want to go that route. What I don't want is a project car, or anything that requires paint, rust repair, or an engine swap. BTDT and paid my dues, frankly. Also, the truck taunts me. I realize these cars are more fun-to-be-seen-in than they are fun-to-drive. Resale, if I choose well, is probably good.
S197 Mustang: I've lusted after a Mustang for an eternity, and this is one of those Life Rewards I think I've earned. But, I don't need a daily driver. They are heavy. It will depreciate. They are not unique. They'll be around a long time. Still want one.
Exocet: I've always wanted to build a car vs restore one. I'd probably have done a Lotus 7 replica by now if CMC hadn't gone belly up years ago. The Birkins and Caterhams are too expensive. I'm also not in love with the 7 looks. Having seen the Exocet last week, however, that kit car lust has resurfaced. Priced right, easy to build while still calling on some creativity. Horribly impractical when completed, and if I'd ever want to sell it...who knows if I even could? Looks like a grin-inducing piece of fun if there ever was one. Possibly would make the BMW redundant.
The Least Sexy Option: spend it on fixing up the truck. Wouldn't take all the cash, but would probably halve it at least. And/or replace the heavy steel trailer with an aluminum one. Practical choices aren't sexy though.
As age 50 appears on the horizon, I'm realizing the available time left in my lifespan means I have to limit some of the dreams and choices floating around in my head. Though I don't necessarily make decisions based on internet strangers, what might help is opinions that bring to light things I had not considered. So, do your worst (and don't just say to any one thing "Do it!". That's not helpful).