Help me be smart, or not: Car Maths

Hello All,

Forgive me if this is long winded and rambling.

I have been lurking for quite awhile and have really come to value the hives knowledge and decision making. 

With that said I need some input on the solution to my car equation. This is somewhat philosophical as I am trying to temper my rampant addiction with some somewhat smart financial thinking. I am currently driving a financed 2014 Wrangler but it is no longer the solution that it once was. 

The basic premise is I am in search of a two cars...I think, but I cannot for the life of me come to a decision that doesn't change every other day. 

The variables for my equation as are follows:

1. I have recently gotten a new job and am on the road across the Midwest at least twice a week, this includes traveling with clients. I am on track to drive around 25k this year. 

2. I have two 150lb malamutes that are in and out of my current car, therefore lots and lots of dog hair, dirt, and slobber.

3. I occasionally (a dozen times a year maybe) need to tow an 18ft boat and a small motorcycle trailer.

4. I want back into something that I can track a couple times a year, or autocross or rallycross (I have no desire to win, I just want to go to events and have fun)

With all that in mind I am looking to GRM to help with how to split duties across two cars in a way that makes sense.

Do I finance a 2012+ silverado or f-150 and then pick up a cheap miata/civic/etc?

Do I get a cheap beater suv/truck for dog and towing duty and then finance something for a highway cruiser/fun car?

Do I go cheap on both cars and not live with a car payment?

If I financed I wouldn't want to really go over 20k-ish.

Someone save me from this endless game of back and forth, what would you do?

Ive only had car payments twice. Hated it.

However, driving 50k a year for a lovong requires me to have a fleet of beaters three deep to guarantee that i can earn a living. The beaters necessitates time outside of work away from the family for repair and maintenance. 

The advent of a company car that never needs anything is a godsend for me. 

Buy something late model for the work car. 3010-2012 impalas are at the bottom of the depreciation curve anx big enough for 4 adults and comfortable.  Get a good one.

Then a cgeap miata.

In reply to Dusterbd13 :

I would love to if I didnt need the ability to cart around 300lbs worth of fur and drool.

Thats why I am leaning towards a truck, bed cap and the dogs are free to get it as messy as they want. 

I like the impala for highway duty, truck/suv for everything else. If you need a toy find a cheap miata when you can afford it. This will keep you away from financing (most likely) and not make you have to drive a truck all the time. Used expeditions are dirt  cheap. 

Saab SUV aka the Tahoe SS?

Haul malamutes, ass and cruise in relative comfort.

Pick up a fun project that you can tow behind or drive short distances and enjoy.

I'd prioritize fuel efficiency, comfort, and appearance for your work vehicle. Something that can be presentable for clients, knock down 30mpg hwy, and not rattle your brains out the whole time while doing that. Something like a V6 or Ecoboost Mustang, or comparable Camaro might fit the bill and come in under budget pretty easily. And they're capable of sporting activities and have sizeable OEM and aftermarket support. If you need 4 doors, a Focus or Fiesta ST, VW GTI, etc would give you the sportiness you're looking for in a versatile hatchback configuration but might be a bit more taxing for you on your long drives.

Then, buy a cheap suburban or truck for towing/dog hauling.

What kind of mileage does a Transit Connect get? Haul dogs and other stuff, use as commuter as well when needed?

Buy Mazda 2 and commute with that as well as autocross it. I do this.

This sounds like 2 cars and a tow rig to me.  Miata-ish thing for fun and not too expensive, car for hauling around clients for business, etc., and a tow rig for the dogs and trailers.  The business vehicle needs to be kinda nice.  LS430-ish.  The Miata-ish MR2 thing can be reasonable.  The tow rig can be a beater but reliable, like a LX470, older Tundra, 4 Runner or T100.  I suggest "no payments" but if you need something for work and don't have anything saved, well, I suppose that could be financed.  You get paid miles, right?

W124 estate, done.

Any GM W-body with a 3.8 V6 in it for a highway mile machine. e.g. Pontiac Grand Prix, Chevy Monte Carlo, Buick LaCrosse, Chevy Impala, etc.  Big comfy cars that eat up miles, are at the bottom of the depreciation curve and will pull high 20s mpg on the highway. If you get one newer than a 2005 you are guaranteed to have the Series 3 3800 V6 which fixed all of the intake manifold woes the earlier ones did.  GM timing chain V6s can be problematic since GM is still trying to learn how timing chain guides wear and steel is a ductile and stretchy metal.

I had a 2008 Grand Prix I bought with 230k on the clock. The guy I bought it from commuted from southern Wisconsin to North Dakota twice a month for 4 years.  I put almost 20k on it in a year and only had to change the oil and the original spark plugs in the time I owned it.   I inherited a Dodge Magnum with 150k less miles so I sold the Grand Prix.  I checked the VIN a couple weeks ago, it's still running around with 270k last reported on it 3 years later.

$4000 buys you the nicest W-body craigslist has to offer.

Another vote for GM W-bodies as great cars for covering a lot of highway distance in comfort and looking at least somewhat presentable while doing it. Add a pickup or truck based SUV for towing / dog duties.

I agree with Dr. Hess that in a perfect world you'd get a luxo/economical cruiser, a toy racecar, and a tow pig. This is reasonable if the all three are cheap, insurance is cheap for 3 or more vehicles I hear. Lexus gs400, miata, and Tahoe.

But you said two cars.

Car: BMW 318/325, Mazda 3, Ford focus ST, c5/c6 corvette, Camaro ss 1le, WRX/any turbo Subaru.

Tow pig: Tahoe (police auction), Yukon, Burban are the usual suspects. 4runner/Tacoma, sequoia/tundra, Lexus gx/lx470.

I'd avoid payments and go vette and Tahoe. Maybe 318 and gx470 or lx470 if you want three row seating.