I drive for rideshare, and I bought this van with 213,000 miles. It had the best service history I've ever seen, 108 records. That gave me confidence because all the Toyota fanboys out there told me well maintained Toyotas go 400,000 miles with almost no issues. It now has 269,000 miles, but it's easily been the worst vehicle I've ever owned. This year alone, I have over $3,000 in repair receipts. Alternator, oil cooler, alignment, front and rear brakes, one CV axle. New battery. Last year, it needed front and rear brakes, the other axle, some suspension work, and a new stereo head unit, among other things. In 2019, the AC compressor (and I bought the van in December 2019) total repair cost including a set of tires: $8,750 (the van only cost $5500 by comparison)

Current issues are as follows. Some may be related to others, but without further ado and in no particular order: 

• Driver power sliding door inop due to broken cable. 
• Van is sluggish to accelerate and only manages 16 MPG (rated for 17/23/20)
• Vibration at highway speed. I know a wheel a bent, but that may not be the only issue. 
• Takes a seriously long time to get cool inside the van on a hot day. Like up to an hour. Cabin filter isn't clogged. 
• Leaking transmission fluid. It appears to be coming from the drain plug, but not confirmed.
• The brake pedal feel and action is wildly inconsistent. Ram the brakes at low speed, and the van doesn't nosedive hard as expected. It also yaws left and right as it's stopping and again once you start to move away again. Ram them at high speed, and the pedal barely travels at all, but the brakes lock up and ABS is ineffective as the van yaws wildly left and right. Gently pushing the brakes, the pedal seems to sink a bit, but doesn't go all the way to the floor. 
• On a very hot day last week, some coolant was pushed out onto my driveway. While running, the van's exhaust wasn't a smooth tone. I could hear a "puff puff puff puff", as if the engine was missing slightly. This seems to be an isolated incident, as I've not been able to replicate it. 
• If you exceed the oil change interval, even by 500 miles, the check engine light, VSC off, and trac off lights all come on. It's a code for cam timing. Changing the oil and clearing the codes "fixes" it. 
• Clunks over bumps and seems to have poorer than expected handling. Sway bar links and front struts were replaced last year. 

On the plus side, the van burns no oil, and doesn't leak any (to my knowledge), it's paid off, the interior is in overall decent shape apart from some minor staining on the carpets. No permanent dash warning lights. 

The problem is in this current market, this is what I'm facing: https://www.cargurus.com/Cars/inventorylisting/viewDetailsFilterViewInventoryListing.action?zip=37013&sellerHierarchyTypes=PAYING_DEALER&showNegotiable=true&sortDir=ASC&sourceContext=usedPaidSearchNoZip&distance=50&sortType=DEAL_SCORE&entitySelectingHelper.selectedEntity=c25998#listing=301024454_isFeatured That's a lot of money for a vehicle I'm really not convinced given my past experience that I can put my trust in for years to come. I'm kind of at a loss for what to do here. I called a shop local to me (Nashville) and they told me there was no question. With the miles, it's time to trade off, but I could fix everything on mine for far less than the hugely inflated cost of a newer one, and I won't be upside down in payments as soon as used prices normalize.