Thanks for all the responses so far - it is also nice to be reminded that there are others with the same general financial perspective (I've been like this passively for a long time, but have only been doing it more actively very recently) who are also car people.
I had not mentioned what the cars themselves were, probably out of some desire for anonymity (if there is anyone who knows me who happens to be reading this, they'd be able to spot me by my cars), but what the hell, I love talking about it.
The Beigemobile is just a 2003 Accord, so what. If it were a manual, I'd be happy to keep it for years, as it's pretty nice to drive except it's a damn automatic and I hate automatics (it's the only one I've ever had - I would not have chosen the car but when I was offered it, a 16k mile Accord for 3/5 its market value was too good an opportunity to pass up to replace my 185k mile G20t that I had already decided to replace with something younger) It has required a set of tires, an alternator, and two batteries. It will need another damn set of tires (they're cupped), front rotors, fluid changes and an A/C leak fixed.
The Japanese car is a '93 Sentra SE-R. It is the most reliable piece of machinery I've owned - until the starter died at ~180k, it needed no more than regular maintenance and consumables (and it got a few modifications, too). It has a completely rust-free body, too. This is getting new rod bearings and since I'm pulling the engine I will probably reseal the front cover, replace a leaking PS hose, replace the steering rack boots, probably the outer CV boots, clean everything up so it looks semi-purty under the hood again. Also replace the rear brakes (rotors and calipers), a sagging door hinge and a couple of other things I can't remember. I already have all parts needed. With a really thorough go-over this could serve primary-car duty again (in a typical year I put about 4-5k on my bikes and 5-8k on my car) though I would really miss things like folding seatbacks. Since I have a set of snow tires and the car has a viscous LSD, it is great in the snow.
The convertible is a Fiat Spider. It's a Turbo, which is quite rare, and which would make it rather more valuable than a regular Spider if it were in really nice condition. It needs rust repair (two high-priority spots on the floor, everything else is "whenever" since I don't care about driving an ugly car), control arms, brake rotors, plugs/wires/dist/vacuum advance, timing belt, Guibo, U-joint and center support bearing, rebuilt steering box, and some other things I'm forgetting. If it's mechanically solid, I'm happy to drive it with the body and interior it has for years. This car typically gets driven no more than a few hundred miles a year, though in part this has been because of its condition.
The Beigemobile is the car that I drive nearly all the time, but is booooringzzzz......it is Mustachian in the sense that it is inexpensive, was an unbeatable value at the price, and is reliable and practical enough. For what it is (midsize sedan with a 4-cylinder), it gets crappy fuel economy, as it won't break 30mpg unless I take the roof rack off completely and keep it under 70. By cotnrast, its predecessors broke 30mpg effortlessly.) As much as I would love an Elise, I do not want to take 800-mile road trips in one, and I can't fit a couple of bikes and a weekend's worth of stuff in one :) So there is a strong case for keeping it. But why punish myself by making the car I drive 99.5% of the time a boringmobile?? I have been casually shopping for a replacement, but have yet yo be convinced enough to be swayed to pull the trigger (I have been sort of seduced by its low mileage) on something else in the $6k-9k range (I'd probably get 8-something selling the Honda.) Candidates include Audi A4s (B6, preferably Avants), Mk V VW GTIs or TDIs, Audi A3s, Mazda 3 hatchbacks and Mazda 6 hatchbacks or wagons, all with manuals. Unfortunately lot of what I like (e.g. a BMW E46 Touring with under 100k, manual, sport package and sunroof) is unicorny.
To FunStickman's point, if I only had one car it would definitely be one I really liked. Fortunately the other two cars are not money drains beyond the cost of the garage. I have spent about $50 on the SE-R in the past 7 years; the Fiat has seen maybe $800 in parts, insurance is cheap, and registration is practically free, and there is the annual city sticker. I never actually bought either car. I can replace the Accord with something I enjoy the heck out of for the same money, but I have to be careful to avoid anything with too many maintenance needs, as I want that car to be the one that gets an oil change once a year and doesn't need much more.
If nothing else, I am cheap - all of my cars together aren't worth, say, a new Fiesta.
The point about owning something vs. being owned by it is a good one, and one I have thought about. In the last year I have gotten rid of a lot of clutter in my home, in large part thanks to a seriously get-shit-done (and also Mustachian) girlfriend and an open spirit on my part. I sometimes feel owned by my cars, but I'm not sure I'm emotionally ready to give them up yet. But I do sometimes think what it would be like to give up the Fiat, and imagine I might could do it.
I am beginning work on the SE-R now, and would like to have it done (on a leisurely schedule) by the end of summer. I don't want to pay someone else to do it, and while the startup inertia on a project for me is tremendous, I do enjoy doing my own work. Once this is driveable, I will drive it. And maybe I will try selling the Honda then, not buying a replacement for it, and seeing how I like it.
