What options does one have when they reach the end of a car lease but cannot find a good deal at the time of it's end?
Like, do you extend the lease? Return the vehicle and try aiming for a different dealership?
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If you don't live in the rust belt, find you a GM W-body with a 3.8 V6. Pontiac Grand Prix, Buick regal, Chevy Impala, maybe more I don't remember. Cheap to buy, reliable drivetrain, plentiful and cheap parts. Get a double-DIN radio unit with Android Auto/apple car play for that touch of modern convenience, it's super easy to replace yourself even if you aren't super handy. Just look underneath and make sure the rockers aren't rusty (rockers are the part of the car directly underneath the doors, you need to look at them from below the car to see them because there is usually a plastic cover over them).
Going from a 1-2 year old car to a 10-30 year old car is going to be awful.
It is. I don't ever want to be in a situation of handling a car with liable baggage. 10-30 old cars will have a lot of issues going regardless if the body of the vehicle is maintained. If you live in states where they're strict on inspections, you can expect to fail one or another at somepoint. The money piling up to maintain a vehicle that's very old and has a chance of breaking down, is about as feasible as maintaining a boat.
It's smarter to have a vehicle for 2 - 6 years at most if you're leasing it. Financing it, do whatever but people need to understand that if that vehicle being financed is not maintained well, good luck trying to sell it.
It definitely takes some careful scrutiny to find a good one, but I've had my 07 Grand Prix for about 3 years now (in the rust belt even) and in total it has still cost me less than $7k including initial purchase and all repairs. Even if it dies right now I'd say I got my money's worth, considering no car payment since I bought it outright. Although I would consider myself pretty handy and I do most repairs and maintenance myself which saves a ton of money. Maintenance and reliability aside, in my opinion the actual driving experience is as good as if not better than some brand new cars, as long as you do the aforementioned radio mod to get AA/car play. Just an option, and obviously it's a bit of a risk, but it could get you through a year or two to allow you to save up enough for a newer car.
I love my Grand Prix, it has a heads-up display like a frickin fighter jet or something. Very few cars have that even today.